Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol (HCID 64556)

名称と識別子

優先名称: Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol
IUPAC: 1-adamantylmethanol
現地名: 1-ヒドロキシメチルアダマンタン
英語名: 1-Adamantanemethanol
分子式: C11H18O
分子量: 166.26

名称と別名

770-71-8Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolEINECS 212-225-3DTXSID20227818RefChem:899306DTXCID70150309212-225-31-Adamantanemethanoladamantan-1-ylmethanol1-Adamantylmethanol1-(Hydroxymethyl)adamantaneMFCD00074751

名称をさらに表示

1-ヒドロキシメチルアダマンタン1-アダマンタンメタノールアダマンタン-1-メタノール1-アダマンチルメタノール1-アダマンタンメタノル1-アダマンタンメタノ-ル1-(ヒドロキシメチル)アダマンタン1‐アダマンタンメタノール[(3r)-アダマンタン-1-イル]メタノールトリシクロ[3.3.1.13,7]デカン-1-メタノールAKOS BC-06681-amantadinolAdamantanemethanol1-Adamantlcarbinol1-adamantanemetholRARECHEM AQ TC 1004CHEMBRDG-BB 40139301-Adamantylcarbinol

Tricyclo[3.3.1.13,7]decane-1-methanol1-Hydroxymethyladamantane(ADAMANTAN-1-YL)METHANOL3-(Hydroxymethyl)adamantane1-Adamantane Methanoladamantanylmethan-1-oltricyclo[3.3.1.1~3,7~]decane-1-methanol1-Adamantanemethanol (6CI,7CI,8CI); (Adamantan-1-yl)methanol; 1-(Hydroxymethyl)adamantane; 1-Adamantylcarbinol; 1-Adamantylmethanol

データベース識別子

CAS: 770-71-8
PubChem CID: 64556
DTXSID: DTXSID20227818
EC Number: 212-225-3
Nikkaji: J79.946G

物性

構造計算による物性

XLogP: 2.4
極性表面積: 20.2 Å²
水素結合供与体数: 1
水素結合受容体数: 1
回転可能結合数: 1
重原子数: 12
形式電荷: 0
複雑度: 156

物理化学的性質

融点: 114 · 114-117 °C (lit.)
沸点: 234.5 °C · 234.5°C (rough estimate)
比重(密度): 0.8802 · 0.8802 (rough estimate)
屈折率: 1.5 · 1.5000 (estimate)
貯蔵温度: Sealed in dry,Room Temperature
酸解離定数(Pka): 15.51 · 15.51±0.10(Predicted)
外見: 結晶性粉末
色: 白い
水溶解度: 水に不溶。メタノールへの溶解度（ほぼ透明）。
BRN: 1853339 · 1853339
InChI: InChI=1S/C11H18O/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10,12H,1-7H2
InChIKey: MDVGOOIANLZFCP-UHFFFAOYSA-N
SMILES: C12(CO)CC3CC(CC(C3)C1)C2
CAS データベース: 770 · 770-71-8(CAS DataBase Reference)

化学的性質

化学的特性white crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationTricyclo3.3.1.13,7decane-1-methanol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

wgk: 3
hs_code: 29061900
risk_code: 36/37/38
hazard_code: Xi
safety_code: 22-24/25-36-26
hazard_class: IRRITANT
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野 · 3 件

用途有機合成原料。

説明1-Adamantanemethanol acts as guest molecule and forms β-cyclodextrin complexes. It reacts with 3,4,5,6-tetrafluorophthalonitrile to yield 3,4,5,6-tetra-(1-adamantylmethoxy)phthalonitrile.

使用1-Adamantanemethanol was used in the synthesis of axially disubstituted silicon(IV) phthalocyanines. It is used as a reagent in the synthesis of adamantane and noradamantane based histone deacetylase (HDAC) inhibitors for the treatment of cancer. It is also used as a reagent in the synthesis of (1-adamantyl)methyl glycidyl ether, a versatile building block for living polymerization. References Gopalan, B., et al.: Bioorg. Med. Chem. Lett., 23, 2532 (2013); Suzuki, T., et al.: J. Med. Chem., 55, 9562 (2012); Moers, C., et al.: Macromol. Rapid Comm., 35, 1075 (2014)

調製方法

純化方法Dissolve the adamantane in Et2O, wash it with aqueous 0.1N NaOH and H2O, dry over CaCl2, evaporate and recrystallise the residue from aqueous MeOH. [Stetter et al. Chem Ber 92 1629 1959, Beilstein 6 IV 400.]