1-(3-hydroxy-2-methylene)propylcyclohexanol | 66950-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-hydroxy-2-methylene)propylcyclohexanol
• 英文别名: 1-[2-(Hydroxymethyl)prop-2-enyl]cyclohexan-1-ol
• CAS: 66950-88-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: WXIVLJHCJBRVNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxy-2-methylene)propylcyclohexanol 在 <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 以72%的产率得到1-(3-hydroxy-2-methylpropyl)cyclohexanol
  参考文献：
  名称：

  Pronounced enhancement of stereoselectivity in asymmetric hydrogenation of 2-substituted 2-propen-1-ols by transient acylation

  摘要：

  In the hydrogenation using a chiral catalyst, Ru2Cl4[(R)-(+)-BINAP](2)NEt(3), aroylation of the allylic hydroxyl group of 2-(hydroxymethyl)4-hydroxy-4-methyl-1-pentene (2b) and 2-(hydroxy-methyl)-3-(1-hydroxycyclohexyl)-1-propene (3b) resulted in pronounced enhancement of asymmetric induction. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02465-3
• 作为产物：
  描述：

  1-(2-Benzyloxymethyl-allyl)-cyclohexanol 在 lithium 作用下， 以 氨 为溶剂， 生成 1-(3-hydroxy-2-methylene)propylcyclohexanol
  参考文献：
  名称：

  Pronounced enhancement of stereoselectivity in asymmetric hydrogenation of 2-substituted 2-propen-1-ols by transient acylation

  摘要：

  In the hydrogenation using a chiral catalyst, Ru2Cl4[(R)-(+)-BINAP](2)NEt(3), aroylation of the allylic hydroxyl group of 2-(hydroxymethyl)4-hydroxy-4-methyl-1-pentene (2b) and 2-(hydroxy-methyl)-3-(1-hydroxycyclohexyl)-1-propene (3b) resulted in pronounced enhancement of asymmetric induction. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02465-3

文献信息

• Methallyl alcohol dianion additions as the salient feature in a facile synthesis of α-methylene-γ-lactones
  作者：Robert M. Carlson

  DOI：10.1016/s0040-4039(01)85057-7

  日期：——
• γ-Functionalised β-methylene organolithium compounds from 3-chloro-2-(chloromethyl)propene: Synthetic applications
  作者：Diego J Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)80206-4

  日期：1993.1

  The reaction of functionalised methallylic chlorides 1 with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound (Barbier-type conditions) at -78-degrees-C leads, after hydrolysis with water, to the corresponding polyfunctionalised compounds 2. Starting materials 1 are easily available from 3-chloro-2-(chloromethyl)propene by nucleophilic substitution.
• CARLSON R. M., TETRAHEDRON LETT. <TELE-AY>, 1978, NO 2, 111-114
  作者：CARLSON R. M.

  DOI：——

  日期：——
• Pronounced enhancement of stereoselectivity in asymmetric hydrogenation of 2-substituted 2-propen-1-ols by transient acylation
  作者：Hitoshi Shimizu、Yuzo Shimada、Atsuko Tomita、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(96)02465-3

  日期：1997.2

  In the hydrogenation using a chiral catalyst, Ru2Cl4[(R)-(+)-BINAP](2)NEt(3), aroylation of the allylic hydroxyl group of 2-(hydroxymethyl)4-hydroxy-4-methyl-1-pentene (2b) and 2-(hydroxy-methyl)-3-(1-hydroxycyclohexyl)-1-propene (3b) resulted in pronounced enhancement of asymmetric induction. (C) 1997, Elsevier Science Ltd.