(+/-)-(1R,2S,5R)-2-acetyl-1,2-dimethyl-5-vinylcyclohexanol | 119254-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1R,2S,5R)-2-acetyl-1,2-dimethyl-5-vinylcyclohexanol
• 英文别名: 1-[(1S,2R,3R)-3-ethenyl-2-hydroxy-1,2-dimethylcyclohexyl]ethanone
• CAS: 119254-08-9；119324-80-0
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: MDZNYPGWCQNQKK-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol 在 吡啶 、 四(三苯基膦)钯 、 二异丙氧基二氯化钛 、 Bu3SnAlEt2 、 四溴化碳 、 水 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (+/-)-(1R,2S,5R)-2-acetyl-1,2-dimethyl-5-vinylcyclohexanol
  参考文献：
  名称：

  Lewis acid promoted highly diastereoselective desymmetric intramolecular cyclization of allylstannane with a diketone

  摘要：

  The Lewis acid mediated desymmetric intramolecular cyclization of prochiral allylstannyl diketone 1 gave a mixture of two diastereomers 2 and 3. Highly diastereoselective synthesis of each diastereoisomer was accomplished by proper choice of the Lewis acids. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10579-2

文献信息

• Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex
  作者：Takashi Shimada、Naoki Asao、Yoshinori Yamamoto

  DOI：10.1016/s0022-328x(00)00897-4

  日期：2001.4

  The Lewis acid mediated desymmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid.

  路易斯酸介导的前手性烯丙基锡烷基二酮的分子内非对称化（1）给出了两种非对映异构体（2和3）的混合物。每个非对映体的高度非对映合成通过路易斯酸的合适的选择来完成的。还通过使用钯催化剂代替路易斯酸来立体选择性地生产化合物3。
• Chelation control in the intramolecular addition of allylsilanes to carbonyl electrophiles
  作者：Gary A. Molander、Steven W. Andrews

  DOI：10.1016/s0040-4020(01)86642-4

  日期：1988.1
• MOLANDER, GARY A.;ANDREWS, STEVEN W., TETRAHEDRON, 44,(1988) N 13, C. 3869-3888
  作者：MOLANDER, GARY A.、ANDREWS, STEVEN W.

  DOI：——

  日期：——
• Lewis acid promoted highly diastereoselective desymmetric intramolecular cyclization of allylstannane with a diketone
  作者：Takashi Shimada、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(97)10579-2

  日期：1998.1

  The Lewis acid mediated desymmetric intramolecular cyclization of prochiral allylstannyl diketone 1 gave a mixture of two diastereomers 2 and 3. Highly diastereoselective synthesis of each diastereoisomer was accomplished by proper choice of the Lewis acids. (C) 1997 Elsevier Science Ltd. All rights reserved.