(R,E)-oct-1-en-1-D-3-ol | 1607854-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,E)-oct-1-en-1-D-3-ol
• CAS: 1607854-86-3
• 化学式: C₈H₁₆O
• 分子量: 129.207
• InChiKey: VSMOENVRRABVKN-ZFBWWBBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  9.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (R)-(-)-1-辛烯-3-醇 在 lithium aluminium tetrahydride 、 甲烷-d2 作用下， 以 四氢呋喃 为溶剂， 反应 12.75h， 生成 (R,E)-oct-1-en-1-D-3-ol 、 (R,Z)-oct-1-en-1-D-3-ol
  参考文献：
  名称：

  Congested C–C Bonds by Pd-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling, a Mechanism-Guided Solution

  摘要：

  Under the influence of a chiral bidentate diphosphine ligand, the Pd-catalyzed asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1,5-dienes with adjacent stereocenters in high regio- and stereoselectivity. A mechanistic study of the coupling utilizing reaction calorimetry and density functional theory analysis suggests that the reaction operates through an inner-sphere 3,3'-reductive elimination pathway, which is both rate-defining and stereodefining. Coupled with optimized reaction conditions, this mechanistic detail is used to expand the scope of allyl allyl couplings to allow the generation of 1,5-dienes with tertiary centers adjacent to quaternary centers as well as a unique set of cyclic structures.

  DOI：

  10.1021/ja502280w