(-)-4(Z)-(4S,5R)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone | 95343-49-0

• 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
• 英文名称: (-)-4(Z)-(4S,5R)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone
• 英文别名: (-)-4(Z)-(4S,5R)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1ynyl)-3,3,5-trimethylcyclohexanone；(4S,5R)-4-hydroxy-4-((Z)-5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone；(4S,5R)-4-hydroxy-4-[(Z)-5-hydroxy-3-methylpent-3-en-1-ynyl]-3,3,5-trimethylcyclohexan-1-one
• CAS: 95343-49-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: WORLVFQFRWYCAV-CWJQNXGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-4(Z)-(4S,5R)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone 在 盐酸 、 4-甲基苯磺酸吡啶 、 红铝 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 12.0h， 生成 (-)-4(1E,3Z)-(4R,5R)-4-hydroxy-4-(5-hydroxy-3-methyl-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone
  参考文献：
  名称：

  Lamb, Nancy; Abrams, Suzanne R., Canadian Journal of Chemistry, 1990, vol. 68, # 7, p. 1151 - 1162

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(10R)-3,3,8,8,10-pentamethyl-1,5-dioxaspiro<5,5>undecan-9-one 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 1.5h， 生成 (-)-4(Z)-(4S,5R)-4-hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone
  参考文献：
  名称：

  Lamb, Nancy; Abrams, Suzanne R., Canadian Journal of Chemistry, 1990, vol. 68, # 7, p. 1151 - 1162

  摘要：

  DOI：

文献信息

• Inhibitors of a 9-cis epoxycarotenoid dioxygenase
  申请人：Abrams Suzanne R.

  公开号：US20100160166A1

  公开（公告）日：2010-06-24

  A compound of formula (I): wherein: R 1 is —SR 10 , —O—C(O)—R 11 , —NR 12 R 13 , where R 10 is a C 1-8 -alkyl group or a phenyl group unsubstituted or substituted by a C 1-4 -alkyl group, R 11 is a thiophenenyl, furanyl or pyrrolyl group, R 12 is H or a C 1-4 -alkyl group and R 13 is a C 1-8 -alkyl group or a phenyl group unsubstituted or substituted by a C 1-4 -alkyl group; R 2 is H or a C 1-4 -alkyl group; R 3 and R 4 are independently H or C 1-4 -alkyl groups; R 5 and R 6 are independently H, OH or OR 14 , or taken together are ═O, where R 14 is a protecting group; R 7 is H or a C 1-4 -alkyl group; and, R 8 is H, R 9 is OH and R 15 is H, or R 15 is H and R 8 and R 9 taken together are —O—, or R 9 is OH and R 8 and R 15 taken together form a bond; and, R 18 and R 19 are both H, or R 18 and R 19 taken together form a bond, or a plant physiologically acceptable salt thereof is useful for inhibiting 9-cis-epoxycarotenoid dioxygenase (NCED) in a plant or seed and is therefore useful for regulating ABA biosynthesis in the plant or seed.

  公式（I）的化合物：其中：R1为—SR10，—O—C（O）—R11，—NR12R13，其中R10为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R11为噻吩基、呋喃基或吡咯基；R12为H或C1-4-烷基，R13为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R2为H或C1-4-烷基；R3和R4分别为H或C1-4-烷基；R5和R6分别为H、OH或OR14，或者一起为═O，其中R14为保护基；R7为H或C1-4-烷基；R8为H，R9为OH，R15为H，或者R15为H，R8和R9一起为—O—，或者R9为OH，R8和R15一起形成键；R18和R19均为H，或者R18和R19一起形成键，或其植物生理学上可接受的盐对于抑制植物或种子中的9-顺式-环氧类胡萝卜二氧化酶（NCED）是有用的，因此对于调节植物或种子中的ABA生物合成是有用的。
• Synthesis and biological activity of allenic analogues of abscisic acid
  作者：Suzanne R. Abrams、B.V. Milborrow

  DOI：10.1016/0031-9422(91)83174-j

  日期：1991.1

  Abstract Novel allenic analogues of abscisic acid (ABA) were synthesized and tested for ABA activity. The allene functional group was introduced by one of two methods: base catalysed isomerization of an enyne to an enallene conjugated to a ketone, or reduction of a 2-butyn-1,4-diol to an allenic alcohol. A 3:1 mixture of ( E )- and ( Z )-3-methyl-5-(4′,4′-ethylenedioxy-2′,6′,6′-trimethylcyclohex-2′-en-1′-ylidene)-2

  摘要 合成了脱落酸 (ABA) 的新型等离子类似物并测试了 ABA 活性。丙二烯官能团通过以下两种方法之一引入：碱催化的烯炔异构化为与酮共轭的烯丙烯，或将 2-丁炔-1,4-二醇还原为丙二烯醇。( E )- 和 ( Z )-3-methyl-5-(4',4'-ethylenedioxy-2',6',6'-trimethylcyclohex-2'-en-1'-ylidene 的 3:1 混合物)-2,4,5-戊三烯酸强烈抑制无菌浮萍 (Lemna gibba) 的生长，在连续光照下 60 μg 1 -1 超过 7 天，导致叶数减少 50%。外消旋ABA在130 μ 1 -1 处引起相同的抑制。这种混合物导致产生类似 turion 的结构，迄今为止已知这种效应仅由短光周期或特定浓度的 ABA 引起。
• Use of compounds to enhance synchrony of germination and emergence in
  申请人：National Research Council of Canada

  公开号：US05518995A1

  公开（公告）日：1996-05-21

  The present invention relates to a composition for enhancing synchrony of germination and emergence in plants and comprises an effective amount of a compound having the following general formula (I); ##STR1##

  本发明涉及一种用于增强植物萌发和出苗同步性的组合物，包括具有以下一般化学式(I)的化合物的有效量；##STR1##
• Abscisic acid-related plant growth regulators - germination promoters
  申请人：Her Majesty the Queen in right of Canada, as represented by the National

  公开号：US05201931A1

  公开（公告）日：1993-04-13

  Composition for enhancing germination and growth of plants which comprises an effective amount of at least one abscisic acid-related compound having the following formula (I): ##STR1##

  该组合物用于促进植物萌发和生长，其包含有效量的至少一种具有以下化学式（I）的脱落酸相关化合物： ##STR1##
• Sesquiterpene-like inhibitors of a 9-cis-epoxycarotenoid dioxygenase regulating abscisic acid biosynthesis in higher plants
  作者：Jason Boyd、Yuanzhu Gai、Ken M. Nelson、Erica Lukiwski、James Talbot、Mary K. Loewen、Stacey Owen、L. Irina Zaharia、Adrian J. Cutler、Suzanne R. Abrams、Michele C. Loewen

  DOI：10.1016/j.bmc.2009.01.076

  日期：2009.4

  Abscisic acid (ABA) is a carotenoid-derived plant hormone known to regulate critical functions in growth, development and responses to environmental stress. The key enzyme which carries out the first committed step in ABA biosynthesis is the carotenoid cleavage 9-cis-epoxycarotenoid dioxygenase (NCED). We have developed a series of sulfur and nitrogen-containing compounds as potential ABA biosynthesis inhibitors of the NCED, based on modification of the sesquiterpenoid segment of the 9-cis-xanthophyll substrates and product. In in vitro assays, three sesquiterpene-like carotenoid cleavage dioxygenase (SLCCD) inhibitor compounds 13, 17 and 18 were found to act as inhibitors of Arabidopsis thaliana NCED 3 (AtNCED3) with K-i'S of 93, 57 and 87 mu M, respectively. Computational docking to a model of AtNCED3 supports a mechanism of inhibition through coordination of the heteroatom with the non-heme iron in the enzyme active site. In pilot studies, pretreatment of osmotically stressed Arabidopsis plants with compound 13 resulted lower levels of ABA and catabolite accumulation compared to levels in mannitol-stressed plant controls. This same inhibitor moderated known ABA-induced gene regulation effects and was only weakly active in inhibition of seed germination. Interestingly, all three inhibitors led to moderation of the stress-induced transcription of AtNCED3 itself, which could further contribute to lowering ABA biosynthesis in planta. Overall, these sesquiterpenoid-like inhibitors present new tools for controlling and investigating ABA biosynthesis and regulation. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.