8-(3-hydroxy-1-propynyl)-7,9,9-trimethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol | 157784-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(3-hydroxy-1-propynyl)-7,9,9-trimethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol
• CAS: 157784-75-3
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: BTFAXJZYHOTADU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-(3-hydroxy-1-propynyl)-7,9,9-trimethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol 在 palladium/alumina 吡啶 、 氢氧化钾 、 氢气 、 4-甲基苯磺酸吡啶 、 对甲苯磺酰氯 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 25.5h， 生成 6,10,10-trimethyl-1-oxaspiro<4.5>deca-3,6-dien-8-one
  参考文献：
  名称：

  Weyerstahl, Peter; Meisel, Thomas, Liebigs Annalen der Chemie, 1994, # 4, p. 415 - 428

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-3-(1'-hydroxy-4',4'-ethylenedioxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-2-butynol tert-butyldiphenylsilyl ether 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以0.49 g的产率得到8-(3-hydroxy-1-propynyl)-7,9,9-trimethyl-1,4-dioxaspiro<4.5>dec-6-en-8-ol
  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

文献信息

• Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity
  作者：Kotomi Ueno、Yoshiharu Araki、Nobuhiro Hirai、Shigeki Saito、Masaharu Mizutani、Kanzo Sakata、Yasushi Todoroki

  DOI：10.1016/j.bmc.2005.03.015

  日期：2005.5

  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.
• Weyerstahl, Peter; Meisel, Thomas, Liebigs Annalen der Chemie, 1994, # 4, p. 415 - 428
  作者：Weyerstahl, Peter、Meisel, Thomas

  DOI：——

  日期：——