(+/-)-3-(1'-hydroxy-4',4'-ethylenedioxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2-butynol tert-butyldiphenylsilyl ether | 855698-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-(1'-hydroxy-4',4'-ethylenedioxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2-butynol tert-butyldiphenylsilyl ether
• CAS: 855698-84-9
• 化学式: C₃₀H₃₈O₄Si
• 分子量: 490.715
• InChiKey: ZODCPJXZBMQDTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(1'-hydroxy-4',4'-ethylenedioxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2-butynol tert-butyldiphenylsilyl ether 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 (-)-6-nor-abscisic acid
  参考文献：
  名称：

  Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity

  摘要：

  A major catabolic enzyme of the plant hormone abscisic acid (ABA) is the cytochrome P450 monooxygenase ABA 8 '-hydroxylase. For designing a specific inhibitor of this enzyme, the substrate specificity and inhibition of CYP707A3, an ABA 8 '-hydroxylase from Arabidopsis thaliana, was investigated using 45 structural analogues of ABA and compared to the structural requirements for ABA activity. Substrate recognition by the enzyme strictly required the 6 '-methyl groups (C-8 ' and C-9 ') which were unnecessary for ABA activity, whereas elimination of the 3-methyl (C-6) and V-hydroxyl groups, which significantly affected ABA activity, had little effect on the ability of analogues to competitively inhibit the enzyme. Fluorination at C-8 ' and C-9 ' resulted in resistance to 8 '-hydroxylation and competitive inhibition of the enzyme. In particular, 8 ',8 '-difluoro-ABA and 9 ',9 '-difluoro-ABA yielded no enzyme reaction products and strongly inhibited the enzyme (K-1 = 0.16 and 0.25 mu M, respectively). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.015
• 作为产物：
  描述：

  7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 、 tert-butyl(diphenyl)(2-propynyloxy)silane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以92%的产率得到(+/-)-3-(1'-hydroxy-4',4'-ethylenedioxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2-butynol tert-butyldiphenylsilyl ether
  参考文献：
  名称：

  Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity

  摘要：

  A major catabolic enzyme of the plant hormone abscisic acid (ABA) is the cytochrome P450 monooxygenase ABA 8 '-hydroxylase. For designing a specific inhibitor of this enzyme, the substrate specificity and inhibition of CYP707A3, an ABA 8 '-hydroxylase from Arabidopsis thaliana, was investigated using 45 structural analogues of ABA and compared to the structural requirements for ABA activity. Substrate recognition by the enzyme strictly required the 6 '-methyl groups (C-8 ' and C-9 ') which were unnecessary for ABA activity, whereas elimination of the 3-methyl (C-6) and V-hydroxyl groups, which significantly affected ABA activity, had little effect on the ability of analogues to competitively inhibit the enzyme. Fluorination at C-8 ' and C-9 ' resulted in resistance to 8 '-hydroxylation and competitive inhibition of the enzyme. In particular, 8 ',8 '-difluoro-ABA and 9 ',9 '-difluoro-ABA yielded no enzyme reaction products and strongly inhibited the enzyme (K-1 = 0.16 and 0.25 mu M, respectively). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.015