5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one | 223798-14-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one
• 英文别名: [(2R,6R,7R,10S,12R,13R,14R)-13-(methoxymethoxy)-4,4,7,17,18,18-hexamethyl-11-methylidene-16-oxo-3,5-dioxatetracyclo[12.3.1.02,6.07,12]octadec-1(17)-en-10-yl] (E)-3-phenylprop-2-enoate
• CAS: 223798-14-9
• 化学式: C₃₄H₄₄O₇
• 分子量: 564.719
• InChiKey: JEFKZZPJCOUCMB-IKDDGQABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 29.0h， 以92%的产率得到9α,10β-(dimethylmethylenedioxy)-5α-hydroxy-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one
  参考文献：
  名称：

  An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells

  摘要：

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.

  DOI：

  10.1021/np020240n
• 作为产物：
  描述：

  2α-acetoxy-5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)taxa-4(20),11-dien-13-one 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one
  参考文献：
  名称：

  An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells

  摘要：

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.

  DOI：

  10.1021/np020240n

文献信息

• An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells
  作者：Shujun Zhang、Jinlan Wang、Katutoshi Hirose、Masayoshi Ando

  DOI：10.1021/np020240n

  日期：2002.12.1

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.