4-[(1R,2S,5R)-menthyloxy]-3,5-diphenyl-1,2,3,5,6,7-hexahydro-3a,4a-diaza-4-phosphacyclopenta[def]phenanthrene 4-sulfide | 916900-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[(1R,2S,5R)-menthyloxy]-3,5-diphenyl-1,2,3,5,6,7-hexahydro-3a,4a-diaza-4-phosphacyclopenta[def]phenanthrene 4-sulfide
• 英文别名: (2S,11S)-15-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2,11-diphenyl-15-sulfido-1,12-diaza-15-phosphoniatetracyclo[10.2.1.05,14.08,13]pentadeca-5(14),6,8(13)-triene
• CAS: 916900-89-5
• 化学式: C₃₄H₄₁N₂OPS
• 分子量: 556.752
• InChiKey: YVCRJMPCVBUPBL-BTEWRAJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(1R,2S,5R)-menthyloxy]-3,5-diphenyl-1,2,3,5,6,7-hexahydro-3a,4a-diaza-4-phosphacyclopenta[def]phenanthrene 4-sulfide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以77%的产率得到(-)-(2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline
  参考文献：
  名称：

  Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes

  摘要：

  Variously substituted 1,10-phenanthrolines are reduced to octahydrophenanthrolines in moderate to good yields with NaBH3CN in acetic acid/methanol. The exact solvent composition is important to avoid the formation of tetrahydrophenanthrolines and N-alkylated by-products, and to optimize the formation of octabydrophenanthrolines. Resolution of a racemic reduction product gives an enantiornerically pure C-2-symmetric diamine from which the corresponding rigid benzimidazolylidene is prepared, whereas reduction of chiral phenanthrolines derived from bicyclic ketones affords diastercomerically pure diamines, which may also be converted to benzimidazolylidenes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.023
• 作为产物：
  描述：

  2,9-二苯基-1,10-菲咯啉 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二甲基苯胺 、 三氯化磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.42h， 生成 4-[(1R,2S,5R)-menthyloxy]-3,5-diphenyl-1,2,3,5,6,7-hexahydro-3a,4a-diaza-4-phosphacyclopenta[def]phenanthrene 4-sulfide
  参考文献：
  名称：

  Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes

  摘要：

  Variously substituted 1,10-phenanthrolines are reduced to octahydrophenanthrolines in moderate to good yields with NaBH3CN in acetic acid/methanol. The exact solvent composition is important to avoid the formation of tetrahydrophenanthrolines and N-alkylated by-products, and to optimize the formation of octabydrophenanthrolines. Resolution of a racemic reduction product gives an enantiornerically pure C-2-symmetric diamine from which the corresponding rigid benzimidazolylidene is prepared, whereas reduction of chiral phenanthrolines derived from bicyclic ketones affords diastercomerically pure diamines, which may also be converted to benzimidazolylidenes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.023

文献信息

• Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes
  作者：Costa Metallinos、Fred B. Barrett、Yao Wang、Shufen Xu、Nicholas J. Taylor

  DOI：10.1016/j.tet.2006.09.023

  日期：2006.11

  Variously substituted 1,10-phenanthrolines are reduced to octahydrophenanthrolines in moderate to good yields with NaBH3CN in acetic acid/methanol. The exact solvent composition is important to avoid the formation of tetrahydrophenanthrolines and N-alkylated by-products, and to optimize the formation of octabydrophenanthrolines. Resolution of a racemic reduction product gives an enantiornerically pure C-2-symmetric diamine from which the corresponding rigid benzimidazolylidene is prepared, whereas reduction of chiral phenanthrolines derived from bicyclic ketones affords diastercomerically pure diamines, which may also be converted to benzimidazolylidenes. (c) 2006 Elsevier Ltd. All rights reserved.