((3aR,7aR)-2,2-Dimethyl-tetrahydro-benzo[1,3]dioxol-3a-yl)-acetonitrile | 210101-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,7aR)-2,2-Dimethyl-tetrahydro-benzo[1,3]dioxol-3a-yl)-acetonitrile
• 英文别名: 2-[(3aR,7aR)-2,2-dimethyl-5,6,7,7a-tetrahydro-4H-1,3-benzodioxol-3a-yl]acetonitrile
• CAS: 210101-07-8
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: GEUMZNNPWRTGDC-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((3aR,7aR)-2,2-Dimethyl-tetrahydro-benzo[1,3]dioxol-3a-yl)-acetonitrile 在 盐酸 、 正丁基锂 、 二异丁基氢化铝 、 三苯基膦 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 29.0h， 生成 (2R)-2-hydroxy-2-(3-trimethylsilylprop-2-ynyl)cyclohexan-1-one
  参考文献：
  名称：

  Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

  摘要：

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00144-x
• 作为产物：
  描述：

  1-环己烯乙腈 在 四氧化锇 、 甲基磺酰胺 、 AD-mix-β 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 9.5h， 生成 ((3aR,7aR)-2,2-Dimethyl-tetrahydro-benzo[1,3]dioxol-3a-yl)-acetonitrile
  参考文献：
  名称：

  Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

  摘要：

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00144-x

文献信息

• Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation
  作者：Jean-Michel Devaux、Jacques Goré、Jean-Michel Vatèle

  DOI：10.1016/s0957-4166(98)00144-x

  日期：1998.5

  The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.