(2R,4R)-4-(5,5-Dimethyl-cyclohepta-1,3,6-trienyloxy)-pentan-2-ol | 413579-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-4-(5,5-Dimethyl-cyclohepta-1,3,6-trienyloxy)-pentan-2-ol
• 英文别名: (2R,4R)-4-[(5,5-Dimethylcyclohepta-1,3,6-trien-1-yl)oxy]pentan-2-ol；(2R,4R)-4-(5,5-dimethylcyclohepta-1,3,6-trien-1-yl)oxypentan-2-ol
• CAS: 413579-39-2
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: HKRJTTLXPXXZOG-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-4-(5,5-Dimethyl-cyclohepta-1,3,6-trienyloxy)-pentan-2-ol 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 生成 2-Diazo-3-oxo-butyric acid (1R,3R)-3-(5,5-dimethyl-cyclohepta-1,3,6-trienyloxy)-1-methyl-butyl ester
  参考文献：
  名称：

  通过化学、区域和立体选择性环丙烷化和立体定向重排不对称合成宝石-二甲基环丙烷稠合化合物

  摘要：

  通过串联反应合成了具有光学活性的 gem-二甲基环丙烷稠合化合物，该反应包括 4-取代的 7,7-二甲基环庚三烯与内部重氮酯的化学-、区域-和立体选择性环丙烷化反应，然后进行立体定向重排。

  DOI：

  10.1246/cl.2003.128

文献信息

• Application of modified hydroxyl-directed diastereodifferentiating Simmons–Smith reaction to an unreactive conjugated triene. Stereocontrolled tandem cyclopropanation–Cope rearrangement–cyclopropanation
  作者：Takahiro Tei、Takashi Sugimura、Toshifumi Katagiri、Akira Tai、Tadashi Okuyama

  DOI：10.1016/s0957-4166(01)00479-7

  日期：2001.10

  The procedure for the hydroxvl-directed zinc carbenoid addition was applied to a one-pot tandem cyclopropanation-Cope rearrangement-cyclopropanation of a cycloheptatriene derivative to afford a stereochemically pure tricyclic compound in high yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
• [6+2] Cycloaddition of N -phenyltriazolinedione with cycloheptatriene derivatives mediated and stereodirected by a chiral 3-oxy substituent
  作者：Takashi Sugimura、Chun Young Im、Tadashi Okuyama

  DOI：10.1016/j.tetlet.2003.12.044

  日期：2004.2

  The addition of N-phenyltriazolinedione to a 7,7-dimethylcycloheptatriene derivative afforded a [6+2] adduct, which was found to be produced by the rearrangement of an initially formed [4+2] adduct. The regioselectivity of the initial addition was controlled by the 3-oxy-substituent, which also mediates the PTAD addition to the tropilidene form. The chiral 3-substituent also controlled the stereoselectivity of the addition to a high degree. (C) 2003 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of<i>gem</i>-Dimethylcyclopropane-fused Compounds through Chemo-, Regio-, and Stereoselective Cyclopropanation and Stereospecific Rearrangement
  作者：Takashi Sugimura、Takahiro Tei、Tadashi Okuyama

  DOI：10.1246/cl.2003.128

  日期：2003.2

  Optically active gem-dimethylcyclopropane-fused compound was synthesized by a tandem reaction consisting of chemo-, regio-, and stereoselective cyclopropanation of a 4-substituted 7,7-dimethylcycloheptatriene with an internal diazo ester and following stereospecific rearrangement.

  通过串联反应合成了具有光学活性的 gem-二甲基环丙烷稠合化合物，该反应包括 4-取代的 7,7-二甲基环庚三烯与内部重氮酯的化学-、区域-和立体选择性环丙烷化反应，然后进行立体定向重排。