((1S,6S)-6-(cyanomethyl)cyclohex-3-en-1-yl)methyl acetate | 1356956-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((1S,6S)-6-(cyanomethyl)cyclohex-3-en-1-yl)methyl acetate
• CAS: 1356956-18-7
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: RFTXPGACYAEVGU-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((1S,6S)-6-(cyanomethyl)cyclohex-3-en-1-yl)methyl acetate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 23.25h， 生成 (4aS,8aS)-1,4,4a,5,8,8a-Hexahydro-3H-2-benzopyran-3-one
  参考文献：
  名称：

  Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

  摘要：

  The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.

  DOI：

  10.1021/ja3111626
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 吡啶 、 potassium cyanide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 149.5h， 生成 ((1S,6S)-6-(cyanomethyl)cyclohex-3-en-1-yl)methyl acetate
  参考文献：
  名称：

  Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

  摘要：

  The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.

  DOI：

  10.1021/ja3111626

文献信息

• Total Synthesis of (+)-Scholarisine A
  作者：Gregory L. Adams、Patrick J. Carroll、Amos B. Smith

  DOI：10.1021/ja211840k

  日期：2012.3.7

  An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.