(4R)-1,4-dimethyl-4,5,6,7-tetrahydro-2H-isoindole | 1427330-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (4R)-1,4-dimethyl-4,5,6,7-tetrahydro-2H-isoindole
• CAS: 1427330-07-1
• 化学式: C₁₀H₁₅N
• 分子量: 149.236
• InChiKey: JWBFQSQBKYOIOR-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4R)-1,4-dimethyl-4,5,6,7-tetrahydro-2H-isoindole 、 4-甲氧基-2,2'-联吡咯-5-甲醛 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-cycloprodigiosin hydrochloride
  参考文献：
  名称：

  Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture

  摘要：

  The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schollkopf-Barton-Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared Material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cyclo-prodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.

  DOI：

  10.1021/acs.orglett.5b01527
• 作为产物：
  描述：

  (7R)-7-methyl-9-(trimethylsilyl)nona-2,8-diyn-4-ol 在 lithium aluminium tetrahydride 、 噻吩-2-甲酸亚铜(I) 、 辛酸铑 、 二乙二醇二甲醚 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 46.59h， 生成 (4R)-1,4-dimethyl-4,5,6,7-tetrahydro-2H-isoindole
  参考文献：
  名称：

  Application of In Situ-Generated Rh-Bound Trimethylenemethane Variants to the Synthesis of 3,4-Fused Pyrroles

  摘要：

  Rh-bound trimethylenemethane variants generated from the interaction of a Rh-carbenoid with an allene have been applied to the synthesis of substituted 3,4-fused pyrroles. The pyrrole products are useful starting points for the syntheses of various dipyrromethene ligands. Furthermore, the methodology has been applied to a synthesis of the natural product cycloprodigiosin, which demonstrates antitumor and immunosuppressor activity.

  DOI：

  10.1021/ja401380d

文献信息

• Application of In Situ-Generated Rh-Bound Trimethylenemethane Variants to the Synthesis of 3,4-Fused Pyrroles
  作者：Erica E. Schultz、Richmond Sarpong

  DOI：10.1021/ja401380d

  日期：2013.3.27

  Rh-bound trimethylenemethane variants generated from the interaction of a Rh-carbenoid with an allene have been applied to the synthesis of substituted 3,4-fused pyrroles. The pyrrole products are useful starting points for the syntheses of various dipyrromethene ligands. Furthermore, the methodology has been applied to a synthesis of the natural product cycloprodigiosin, which demonstrates antitumor and immunosuppressor activity.
• Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
  作者：Rebecca E. Johnson、Tristan de Rond、Vincent N. G. Lindsay、Jay D. Keasling、Richmond Sarpong

  DOI：10.1021/acs.orglett.5b01527

  日期：2015.7.17

  The enantiomers of the natural product cycloprodigiosin were prepared using an expedient five-step synthetic sequence that takes advantage of a Schollkopf-Barton-Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared Material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cyclo-prodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.