4,6-dimethyl-5H-spiro-[bicyclo[4.1.0]hept-3-ene-2,2'-[1,3]dioxolane]-5-one | 113282-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-dimethyl-5H-spiro-[bicyclo[4.1.0]hept-3-ene-2,2'-[1,3]dioxolane]-5-one
• 英文别名: (+/-)-4,4-ethylenedioxy-5,6-methano-2,6-dimethyl-2-cyclohexen-1-one；1',3'-Dimethylspiro[1,3-dioxolane-2,5'-bicyclo[4.1.0]hept-3-ene]-2'-one
• CAS: 113282-72-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: GFXMVXWHBMJXHP-UHFFFAOYSA-N

物化性质

• 沸点：
  306.9±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-5H-spiro-[bicyclo[4.1.0]hept-3-ene-2,2'-[1,3]dioxolane]-5-one 在 manganese(IV) oxide 、 sodium hydroxide 、 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 (-)-5'α,8'-cycloabscisic acid
  参考文献：
  名称：

  Metabolism of 5′α,8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings

  摘要：

  We synthesized 5'alpha,8'-cycloabscisic acid (CycloABA), a highly potent and long-lasting abscisic acid (ABA) analogue, by a different method from that reported before. CycloABA fed to radish seedlings had more metabolic tolerance than ABA. The major metabolite of CycloABA was the glucose conjugate, which was the minor metabolite of ABA. The 8'-hydroxylated metabolite and its cyclized isomer, which were major metabolites of ABA, were not found as metabolites of CycloABA. The present results suggest that the highly potent and long-lasting activity of CycloABA is caused by resistance to ABA 8'-hydroxylase, and that CycloABA is partially metabolized to the glucose conjugate by ABA glucosyltransferase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.048
• 作为产物：
  描述：

  trimethylsulphoxonium iodide 、 4,4-亚乙二氧基-2,6-二甲基-2,5-环己二烯-1-酮 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.25h， 以95%的产率得到4,6-dimethyl-5H-spiro-[bicyclo[4.1.0]hept-3-ene-2,2'-[1,3]dioxolane]-5-one
  参考文献：
  名称：

  Metabolism of 5′α,8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings

  摘要：

  We synthesized 5'alpha,8'-cycloabscisic acid (CycloABA), a highly potent and long-lasting abscisic acid (ABA) analogue, by a different method from that reported before. CycloABA fed to radish seedlings had more metabolic tolerance than ABA. The major metabolite of CycloABA was the glucose conjugate, which was the minor metabolite of ABA. The 8'-hydroxylated metabolite and its cyclized isomer, which were major metabolites of ABA, were not found as metabolites of CycloABA. The present results suggest that the highly potent and long-lasting activity of CycloABA is caused by resistance to ABA 8'-hydroxylase, and that CycloABA is partially metabolized to the glucose conjugate by ABA glucosyltransferase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.048

文献信息

• SUBSTITUTED VINYL AND ALKINYL CYCLOHEXENOLS AS ACTIVE AGENTS AGAINST ABIOTIC STRESS IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140080704A1

  公开（公告）日：2014-03-20

  The invention relates to substituted vinyl- and alkynylcyclohexenols of the general formula (I) and salts thereof where the R 1 , R 2 , R 3 , R 4 , R 5 , [X—Y] and Q radicals are each as defined in the description, to processes for preparation thereof and to the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  该发明涉及通式（I）中的取代乙烯基和炔基环己烯醇及其盐，其中R1、R2、R3、R4、R5、[X—Y]和Q基团如描述中所定义，以及其制备方法和用途，用于增强植物对非生物胁迫的抗逆性，和/或增加植物产量。
• Diels-Alder reactions of vinylbicyclo[4.1.0]heptenes
  作者：Makoto Sakaino、Jerrold Meinwald

  DOI：10.1016/s0040-4039(00)95471-6

  日期：1987.1

  Efficient syntheses of 1,3-dimethy1-2-vinylbicyclo[4.1.0]hept-2-ene (1) and 2,2-ethylenedioxy-4,6-dimethyl-5-vinylbicyclo[4.1.0]hept-4-ene (2) are described. These dienes, which undergo Diels-Alder reactions with -benzoquinones readily, may serve as versatile intermediates for terpenoid synthesis.

  有效合成1,3-二甲基1-2-乙烯基双环[4.1.0]庚-2-烯（1）和2,2-乙烯二氧基-4,6-二甲基-5-乙烯基双环[4.1.0]庚-4-描述了烯（2）。这些二烯容易与-苯醌醌进行狄尔斯-阿尔德反应，可以用作萜类化合物合成的通用中间体。
• SUBSTITUTED 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)PENTA-2,4-DIENES AND 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)PENT-2-ENE-4-INES AS ACTIVE AGENTS AGAINST ABIOTIC STRESSES IN PLANTS
  申请人：Frackenpohl Jens

  公开号：US20140051577A1

  公开（公告）日：2014-02-20

  The invention relates to substituted 5-(bicyclo[4.1.0]hept-3-en-2-yl)penta-2,4-dienes and 5-(bicyclo[4.1.0]hept-3-en-2-yl)pent-2-ene-4-ines of the formula (I) and salts thereof, where the radicals R1, R2, R3, R4, R5, [X—Y] and Q are each as defined in the description, to processes for preparation thereof and to the use thereof for enhancing stress tolerance in plants with respect to abiotic stress, and/or for increasing plant yield.

  该发明涉及代换的5-(bicyclo[4.1.0]庚-3-烯-2-基)戊-2,4-二烯和5-(bicyclo[4.1.0]庚-3-烯-2-基)戊-2-烯-4-炔的化合物及其盐，其中基团R1、R2、R3、R4、R5、[X—Y]和Q的定义如描述中所示，以及其制备方法和用途，用于增强植物对非生物胁迫的抗压能力，和/或增加植物产量。
• SAKAINO, MAKOTO;MEINWALD, JERROLD, TETRAHEDRON LETT., 28,(1987) N 28, 3201-3204
  作者：SAKAINO, MAKOTO、MEINWALD, JERROLD

  DOI：——

  日期：——
• SUBSTITUIERTE 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)-PENTA-2,4-DIENE UND 5-(BICYCLO[4.1.0]HEPT-3-EN-2-YL)-PENT-2-EN-4-INE ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2697194A1

  公开（公告）日：2014-02-19