9-二氢紫杉醇 | 148584-53-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 9-二氢紫杉醇
• 英文名称: 9(R)-dihydrotaxol
• 英文别名: 9-Dihydrotaxol；[(1S,2S,3R,4S,7R,9S,10S,11R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9,11-trihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 148584-53-6
• 化学式: C₄₇H₅₃NO₁₄
• 分子量: 855.936
• InChiKey: RIYRAFARMCGSSW-UWNPAEFKSA-N

物化性质

• 沸点：
  957.2±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  62
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  224
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  丙醛 、 9-二氢紫杉醇 在 对甲苯磺酸 作用下， 反应 4.0h， 以62%的产率得到9(R)-dihydrotaxol 7,9-propylidene acetal
  参考文献：
  名称：

  Antitumor Activity of 9(R)-Dihydrotaxane Analogs

  摘要：

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.

  DOI：

  10.1021/jm00009a009
• 作为产物：
  描述：

  7,9-acetonide 13-acetyl-9-dihydrobaccatin III 在 盐酸 、 正丁基锂 、 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 生成 9-二氢紫杉醇
  参考文献：
  名称：

  Synthesis of 9-dihydrotaxol: A novel bioactive taxane

  摘要：

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.

  DOI：

  10.1016/s0040-4039(00)60342-8

文献信息

• Synthesis of 9-dihydrotaxol: A novel bioactive taxane
  作者：Larry L. Klein

  DOI：10.1016/s0040-4039(00)60342-8

  日期：1993.3

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.
• Antitumor Activity of 9(R)-Dihydrotaxane Analogs
  作者：Larry L. Klein、Leping Li、Clarence J. Maring、Clinton M. Yeung、Sheela A. Thomas、David J. Grampovnik、Jacob J. Plattner

  DOI：10.1021/jm00009a009

  日期：1995.4

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.