9-hydroxymegastigma-3,5-dien-7-yne | 79925-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-hydroxymegastigma-3,5-dien-7-yne
• 英文别名: Megastigma-3,5-dien-7-yn-9-ol；3-Butyn-2-ol, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-；4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-yn-2-ol
• CAS: 79925-81-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: ZNBPOSMCKDWSMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-hydroxymegastigma-3,5-dien-7-yne 以 乙醇 、 水 为溶剂， 生成 大马士酮
  参考文献：
  名称：

  Identification of a precursor to naturally occurring β-damascenone

  摘要：

  9-Hydroxymegastigma-3,5-dien-7-yne 8a was synthesised and shown to be identical to an intermediate found in the acid-catalysed conversion of 3,5,9-trihydroxymegastigma-6,7-diene 4 to beta -damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3,9-diol 6. When subjected to acid hydrolysis, 8a produced beta -damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01411-3
• 作为产物：
  描述：

  2,2,6-三甲基环己酮 在 氢氧化钾 、 Celite 、 溴 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 9-hydroxymegastigma-3,5-dien-7-yne
  参考文献：
  名称：

  Identification of a precursor to naturally occurring β-damascenone

  摘要：

  9-Hydroxymegastigma-3,5-dien-7-yne 8a was synthesised and shown to be identical to an intermediate found in the acid-catalysed conversion of 3,5,9-trihydroxymegastigma-6,7-diene 4 to beta -damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3,9-diol 6. When subjected to acid hydrolysis, 8a produced beta -damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01411-3

文献信息

• Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and Their Analogues, in both Aglycone and Glycoconjugate Forms
  作者：Merran A. Daniel、Carolyn J. Puglisi、Dimitra L. Capone、Gordon M. Elsey、Mark A. Sefton

  DOI：10.1021/jf8018134

  日期：2008.10.8

  megastigma-4,6,7-trien-9-ol (7) and megastigma-6,7-dien-9-ol (8) were synthesized. No 1,3-transposition of oxygen to form analogues of damascenone was observed when 7 and 8 were subjected to mild acidic conditions. Such transposition takes place only with highly conjugated acetylenic precursors such as 6 or tertiary allenic alcohols such as 2. The placement of glucose at C-3 of 5 and at C-9 of 6 gave the

  megastigma-4,6,7-trien-3,9-diol（5）和megastigma-3,4-dien-7-yn-9-ol（6）在pH 3.0和3.2的乙醇水溶液中储存仅在室温下为damascenone（1）和damascenone加合物。二醇（5）在pH 3.0和pH 3.2下分别具有32和48小时转化的半衰期。在相同的pH值下，炔醇（6）的半衰期分别为40和65 h。为了研究5和先前研究的烯丙三醇2中C-9羟基官能团的反应性，两种模型化合物megastigma-4,6,7-trien-9-ol（7）和megastigma-6,7合成了-dien-9-ol（8）。当将7和8置于温和的酸性条件下时，未观察到氧的1,3-易位形成大马mas酮的类似物。仅用高度共轭的炔属前体（如6）或叔烯丙醇（如2）进行这种转座。将葡萄糖分别置于C-3为5和C-9为6时分别得到糖苷9和10。这种葡糖缀合的
• Precursors of damascenone in fruit juices
  作者：George K Skouroumounis、Ralph A Massy-Westropp、Mark A Sefton、Patrick J Williams

  DOI：10.1016/s0040-4039(00)92682-0

  日期：1992.6

  The acid catalysed reactions of 6,7-megastigmadiene-3,5,9-triol and the beta-D-glucosides of 5-Megastigmen-7-yne-3,9-diol and 3-hydroxy-beta-damascone have been studied in relation to the formation of damascenone. The results show that hydrolysis of the allene triol could account for damascenone formation in the juices of grapes and other fruits.
• Identification of a precursor to naturally occurring β-damascenone
  作者：Carolyn J Puglisi、Gordon M Elsey、Rolf H Prager、George K Skouroumounis、Mark A Sefton

  DOI：10.1016/s0040-4039(01)01411-3

  日期：2001.9

  9-Hydroxymegastigma-3,5-dien-7-yne 8a was synthesised and shown to be identical to an intermediate found in the acid-catalysed conversion of 3,5,9-trihydroxymegastigma-6,7-diene 4 to beta -damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3,9-diol 6. When subjected to acid hydrolysis, 8a produced beta -damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5. (C) 2001 Elsevier Science Ltd. All rights reserved.