(((1R,4aS,5S,6S,8aR)-5-(2,5-dimethoxybenzyl)-1-hydroxy-5,6-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)methyl)(methylimino)(phenyl)-l6-sulfanone | 305791-29-1

• 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: (((1R,4aS,5S,6S,8aR)-5-(2,5-dimethoxybenzyl)-1-hydroxy-5,6-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)methyl)(methylimino)(phenyl)-l6-sulfanone
• CAS: 305791-29-1
• 化学式: C₂₉H₃₉NO₄S
• 分子量: 497.699
• InChiKey: LLFOQAITXRMAIW-CHHLMABUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.12
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (((1R,4aS,5S,6S,8aR)-5-(2,5-dimethoxybenzyl)-1-hydroxy-5,6-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)methyl)(methylimino)(phenyl)-l6-sulfanone 以 甲苯 为溶剂， 反应 10.0h， 以96%的产率得到(+)-(1R,2S,4aS,8aS)-trans-1β-[(2,5-dimethoxyphenyl)methyl]-1,2,4a,7,8,8a-hexahydro-1α,2β-dimethyl-5(6H)-naphthalenone
  参考文献：
  名称：

  Synthesis of a Potential Key Intermediate of Akaterpin, Specific Inhibitor of PI-PLC

  摘要：

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and tuans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of beta,gamma-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00619-0
• 作为产物：
  描述：

  trans-1α-[(2,5-dimethoxyphenyl)methyl]-1,2,4a,5,6,7,8,8a-octahydro-1β,2α-dimethyl-5α-naphthalenol 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (((1R,4aS,5S,6S,8aR)-5-(2,5-dimethoxybenzyl)-1-hydroxy-5,6-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)methyl)(methylimino)(phenyl)-l6-sulfanone
  参考文献：
  名称：

  Synthesis of a Potential Key Intermediate of Akaterpin, Specific Inhibitor of PI-PLC

  摘要：

  In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and tuans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of beta,gamma-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00619-0

文献信息

• Determination of the Absolute Structure of (+)-Akaterpin
  作者：Hayato Hosoi、Nobuyuki Kawai、Hideki Hagiwara、Takahiro Suzuki、Atsuo Nakazaki、Ken-ichi Takao、Kazuo Umezawa、Susumu Kobayashi

  DOI：10.1248/cpb.60.137

  日期：——

  We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (−)-1 with that of natural akaterpin.

  我们描述了(+)-akaterPIn (1)的完全合成和结构确定，这是一种磷脂酰肌醇特异性磷脂酶C（PI-PLC）的抑制剂。合成策略的关键特征包括使用手性亚砜6拆分β,γ-不饱和酮（±）-2a。通过比较(+)-1和（-）-1与天然akaterPIn的特定旋光数据，确定了绝对立体化学。