rac-(R)-6,6,9-trimethyl-2-tosyl-9-vinyl-6,7,8,9-tetrahydronaphtho[1,2,3-cd]indol-10(2H)-one | 131572-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-(R)-6,6,9-trimethyl-2-tosyl-9-vinyl-6,7,8,9-tetrahydronaphtho[1,2,3-cd]indol-10(2H)-one
• 英文别名: 4-Ethenyl-4,8,8-trimethyl-14-(4-methylphenyl)sulfonyl-14-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),9(16),10,12-pentaen-3-one
• CAS: 131572-81-1
• 化学式: C₂₇H₂₇NO₃S
• 分子量: 445.582
• InChiKey: IGLSXDFOGHXJIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-(R)-6,6,9-trimethyl-2-tosyl-9-vinyl-6,7,8,9-tetrahydronaphtho[1,2,3-cd]indol-10(2H)-one 在 lithium aluminium tetrahydride 、 草酰氯 、 ammonium acetate 、 sodium cyanoborohydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 62.75h， 生成 rac-(6aS,9R,10R,10aS)-6,6,9-trimethyl-9-vinyl-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indol-10-amine
  参考文献：
  名称：

  Total Synthesis of Hapalindoles J and U

  摘要：

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.

  DOI：

  10.1021/jo202139k
• 作为产物：
  描述：

  rac-6-(2-(1-(tert-butyldimethylsilyl)-1H-indol-4-yl)propan-2-yl)-3-methyl-2-((trimethylsilyl)oxy)-3-vinylcyclohexanone 在 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 rac-(R)-6,6,9-trimethyl-2-tosyl-9-vinyl-6,7,8,9-tetrahydronaphtho[1,2,3-cd]indol-10(2H)-one
  参考文献：
  名称：

  Total Synthesis of Hapalindoles J and U

  摘要：

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.

  DOI：

  10.1021/jo202139k

文献信息

• Synthetic studies of marine alkaloids hapalindoles. Part I Total synthesis of (±)-hapalindoles J and M
  作者：Hideaki Muratake、Mitsutaka Natsume

  DOI：10.1016/s0040-4020(01)96005-3

  日期：——

  The first concise synthesis of marine indole alkaloids (±)-hapalindoles J (4) and M (5) was achieved in seven or six steps starting from a readily available compound 6 using important key reactions, 6 → 7 → and 8 and 35 → 41 or 5.

  海洋吲哚生物碱（±）-单吲哚J（4）和M（5）的第一个简明合成是通过使用重要的关键反应6→7→以及8和35→从现成的化合物6开始以七六步完成的41或5。
• Synthetic studies of marine alkaloids hapalindoles. Part 3 Total synthesis of (±)-hapalindoles H and U
  作者：Hideaki Muratake、Harumi Kumagami、Mitsutaka Natsume

  DOI：10.1016/s0040-4020(01)96007-7

  日期：——

  A total, synthesis of marine indole alkaloids (±) -hapalindoles H (1) and U (2) was achieved from the previously described compound 7 by way of 13, 21, and 26 for U (2), and 33 and 32 for H (1).

  总共，合成海洋吲哚生物碱的（±）-hapalindoles H（1）和U（2）是从前面描述的化合物来实现7通过的方式13，21，和26为U（2），和33和32为H（1）。
• Total Synthesis of Hapalindoles J and U
  作者：Ryan J. Rafferty、Robert M. Williams

  DOI：10.1021/jo202139k

  日期：2012.1.6

  The total synthesis of D,L-hapalindoles J and U has been accomplished. Hapalindole J was prepared in 11% overall yield over 11 synthetic steps and hapalindole U was prepared in 25% overall yield over 13 synthetic steps from commercially available materials. The route employs a novel silyl ether-based strategy for accessing the 6:5:6:6 ring system of the hapafindoles rapidly and in good yields.