combretastatin D-1 benzyl ether | 202645-49-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: combretastatin D-1 benzyl ether
• 英文别名: (2R,4S)-13-phenylmethoxy-3,6,15-trioxatetracyclo[14.2.2.110,14.02,4]henicosa-1(19),10(21),11,13,16(20),17-hexaen-7-one
• CAS: 202645-49-6
• 化学式: C₂₅H₂₂O₅
• 分子量: 402.447
• InChiKey: MTVLYTIHOBITLN-UKILVPOCSA-N

物化性质

• 沸点：
  629.9±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  combretastatin D-1 benzyl ether 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 combretastatin D-1-(S)-(O-acetyl) mandelate
  参考文献：
  名称：

  Total Synthesis of Combretastatins D

  摘要：

  The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol, The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+) acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<33::aid-chem33>3.0.co;2-8
• 作为产物：
  描述：

  3-(4-溴苯基)丙-2-烯-1-醇 在 吡啶 、 咪唑 、 potassium osmate 、 lithium hydroxide 、 copper(I) bromide dimethylsulfide complex 、 甲基磺酰胺 、 四丁基氟化铵 、 二异丁基氢化铝 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三苯基膦 、 potassium hexacyanoferrate(III) 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 46.84h， 生成 combretastatin D-1 benzyl ether
  参考文献：
  名称：

  Total Synthesis of Combretastatins D

  摘要：

  The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol, The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+) acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<33::aid-chem33>3.0.co;2-8

文献信息

• Total Synthesis of Combretastatins D
  作者：Elias A. Couladouros、Ioanna C. Soufli、Vassilios I. Moutsos、Raj K. Chadha

  DOI：10.1002/(sici)1521-3765(199801)4:1<33::aid-chem33>3.0.co;2-8

  日期：1998.1

  The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construction of both combretastatins. The synthesis of combretastatin D-2 is completed by the use of Sammuelson's dehydroxylation protocol, The asymmetric epoxide of combretastatin D-1 is constructed in two separate operations: one asymmetric center is fixed at an early stage of the synthetic route by Sharpless AD of a trans-styrene derivative, inducing the intramolecular formation of the asymmetric epoxide at the final stages. The synthesis of the title compounds is accomplished in high overall yields (37% for D-1 and 41% for D-2, 9 steps in both cases). X-ray crystallographic analysis of the (S)-(+) acetylmandelic ester of (-)-combretastatin D-1 verified its revised structure.