(1S,6R,7S,8S)-1,3,5-trimethyl-8-(4-nitrophenyl)bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid | 1351985-46-0

• 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: (1S,6R,7S,8S)-1,3,5-trimethyl-8-(4-nitrophenyl)bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid
• CAS: 1351985-46-0
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: VGARRCDIWZBBOK-CUSZFKRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,6R,7S,8S)-1,3,5-trimethyl-8-(4-nitrophenyl)bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid 、 L-苯甘氨醇 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric Induction in 8π Electrocyclizations. Design of a Removable Chiral Auxiliary

  摘要：

  The pseudo C-2 symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8 pi, 6 pi tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.

  DOI：

  10.1021/ol202932x
• 作为产物：
  描述：

  在 水 、 sodium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1S,6R,7S,8S)-1,3,5-trimethyl-8-(4-nitrophenyl)bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid
  参考文献：
  名称：

  Asymmetric Induction in 8π Electrocyclizations. Design of a Removable Chiral Auxiliary

  摘要：

  The pseudo C-2 symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8 pi, 6 pi tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.

  DOI：

  10.1021/ol202932x

文献信息

• Asymmetric Induction in 8π Electrocyclizations. Design of a Removable Chiral Auxiliary
  作者：Keunsoo Kim、Joseph W. Lauher、Kathlyn A. Parker

  DOI：10.1021/ol202932x

  日期：2012.1.6

  The pseudo C-2 symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8 pi, 6 pi tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with the same helical twist. This assignment prefaces the development of analogs of SNF4435 C and D. These natural products demonstrate activity as androgen receptor antagonists and as multidrug resistance (mdr) reversal agents.