(1R,2R)-2-(7-(tert-butyldiphenylsilyloxy)heptanoyl)-N-methoxy-N-methylcyclopropanecarboxamide | 1293981-35-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2R)-2-(7-(tert-butyldiphenylsilyloxy)heptanoyl)-N-methoxy-N-methylcyclopropanecarboxamide
• 英文别名: (1R,2R)-2-[7-[tert-butyl(diphenyl)silyl]oxyheptanoyl]-N-methoxy-N-methylcyclopropane-1-carboxamide
• CAS: 1293981-35-7
• 化学式: C₂₉H₄₁NO₄Si
• 分子量: 495.734
• InChiKey: YEKQJEHDPDCHJQ-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-(7-(tert-butyldiphenylsilyloxy)heptanoyl)-N-methoxy-N-methylcyclopropanecarboxamide 在 2,6-二甲基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 碘苯二乙酸 、 C₁₀H₁₄*C₁₄H₁₄N₂RuS 、 四丁基氟化铵 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 异丙醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (S)-7-hydroxy-7-((1R,2R)-2-(trityloxymethyl)cyclopropyl)heptanal
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of solandelactone A and B

  摘要：

  A stereocontrolled synthesis of cyclopropyl delta-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol is accomplished with predictable absolute stereochemistry via organocatalytic and catalytic asymmetric transfer hydrogenation reactions. The salient feature of this protocol is the genesis of chirality through an organocatalytic reaction and utilized for installing a critical bifunctional trans-cyclopropane motif, which is a key segment of every representative member of the oxylipin class of natural products such as solandelactone A and B. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.008
• 作为产物：
  描述：

  1,7-庚二醇 在 2-iodoxybenzoic acid 、 hydroquinine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 sodium acetate 、 sodium hydride 、 caesium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 oil 为溶剂， 反应 40.0h， 生成 (1R,2R)-2-(7-(tert-butyldiphenylsilyloxy)heptanoyl)-N-methoxy-N-methylcyclopropanecarboxamide
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of solandelactone A and B

  摘要：

  A stereocontrolled synthesis of cyclopropyl delta-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol is accomplished with predictable absolute stereochemistry via organocatalytic and catalytic asymmetric transfer hydrogenation reactions. The salient feature of this protocol is the genesis of chirality through an organocatalytic reaction and utilized for installing a critical bifunctional trans-cyclopropane motif, which is a key segment of every representative member of the oxylipin class of natural products such as solandelactone A and B. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.008

文献信息

• Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of solandelactone A and B
  作者：Gullapalli Kumaraswamy、Gajula Ramakrishna、Balasubramanian Sridhar

  DOI：10.1016/j.tetlet.2011.02.008

  日期：2011.4

  A stereocontrolled synthesis of cyclopropyl delta-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol is accomplished with predictable absolute stereochemistry via organocatalytic and catalytic asymmetric transfer hydrogenation reactions. The salient feature of this protocol is the genesis of chirality through an organocatalytic reaction and utilized for installing a critical bifunctional trans-cyclopropane motif, which is a key segment of every representative member of the oxylipin class of natural products such as solandelactone A and B. (C) 2011 Elsevier Ltd. All rights reserved.