1,4-Dimethyl-4,5,6,7-tetrahydro-2H-isoindole | 90486-72-9

• 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: 1,4-Dimethyl-4,5,6,7-tetrahydro-2H-isoindole
• CAS: 90486-72-9
• 化学式: C₁₀H₁₅N
• mdl: MFCD19223428
• 分子量: 149.236
• InChiKey: JWBFQSQBKYOIOR-UHFFFAOYSA-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：

  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， 生成 cycloprodigiosin
  参考文献：
  名称：

  The synthesis of (±)-cycloprodigiosin

  摘要：

  DOI：

  10.1016/s0040-4039(01)80165-9
• 作为产物：
  描述：

  3-methyl-1-nitrocyclohex-1-ene 在 叔丁基过氧化氢 、 samarium diiodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙二醇 为溶剂， 反应 42.58h， 生成 1,4-Dimethyl-4,5,6,7-tetrahydro-2H-isoindole
  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

文献信息

• JP2000128876A
  申请人：——

  公开号：JP2000128876A

  公开（公告）日：2000-05-09
• The synthesis of (±)-cycloprodigiosin
  作者：Harry H. Wasserman、James M. Fukuyama

  DOI：10.1016/s0040-4039(01)80165-9

  日期：1984.1
• 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'.