(2R,3R,4aR,8R,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one | 226088-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2R,3R,4aR,8R,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one
• 英文别名: (2R,3R,4aR,8R,8aS)-8-[(6-iodo-1,3-benzodioxol-5-yl)methoxy]-2,3-dimethoxy-2,3-dimethyl-8,8a-dihydro-4aH-1,4-benzodioxin-5-one
• CAS: 226088-82-0
• 化学式: C₂₀H₂₃IO₈
• 分子量: 518.302
• InChiKey: DXDCEJQMSVZOHC-RBUQIHAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,8R,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到(2R,3R,4aS,4bR,11bS,13aR)-2,3-Dimethoxy-2,3-dimethyl-2,3,4a,11b,12,13a-hexahydro-4bH,6H-1,4,5,8,10-pentaoxa-cyclopenta[b]chrysen-13-one
  参考文献：
  名称：

  An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

  摘要：

  In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00334-2
• 作为产物：
  描述：

  2,2,3,3-四甲氧基丁烷 在 2,6-二甲基吡啶 、 草酰氯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 mercury(II) trifluoroacetate 、 sodium hydride 、 二甲基亚砜 、 甲基磺酰氯 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (2R,3R,4aR,8R,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one
  参考文献：
  名称：

  An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

  摘要：

  In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00334-2