2H,3H-环戊二烯并[b]呋喃并[2',3',4':4,5]萘并[2,3-d]呋喃-6-乙酸,8-(3-呋喃基)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-十二氢-3,5-二羟基-2a,5a,6a,7-四甲基-,甲基酯,(2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)- | 1062-24-4

• 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
• 中文名称: 2H,3H-环戊二烯并[b]呋喃并[2',3',4':4,5]萘并[2,3-d]呋喃-6-乙酸,8-(3-呋喃基)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-十二氢-3,5-二羟基-2a,5a,6a,7-四甲基-,甲基酯,(2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)-
• 英文名称: deacetyldetigloylsalannin
• 英文别名: 3-De-O-acetyl-1-de-O-[(E)-2-methylbut-2-enoyl]salannin；methyl nimbidate；3-deacetyl-1-detigloylsalannin；2H,3H-Cyclopenta(d')naphtho(1,8-bc:2,3-b')difuran-6-acetic acid, 8alpha-(3-furyl)-2a,4,5,5a,6alpha,6a,8,9,9aalpha,10abeta,10bbeta,10calpha-dodecahydro-3alpha,5alpha-dihydroxy-2abeta,5abeta,6abeta,7-tetramethyl-, methyl ester；methyl 2-[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-12,14-dihydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-10-yl]acetate
• CAS: 1062-24-4
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: VQEGVEGIYONFAK-GUWVMMNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2H,3H-环戊二烯并[b]呋喃并[2',3',4':4,5]萘并[2,3-d]呋喃-6-乙酸,8-(3-呋喃基)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-十二氢-3,5-二羟基-2a,5a,6a,7-四甲基-,甲基酯,(2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)- 生成 1-O-acetyldeacetyldetigloylsalannin
  参考文献：
  名称：

  LEY, STEVEN V.;ANDERSON, JAMES C.;BLANEY, WALLY M.;JONES, PHILIP S.;LIDER+, TETRAHEDRON, 45,(1989) N6, C. 5175-5192

  摘要：

  DOI：
• 作为产物：
  描述：

  印楝沙兰林 在 苄基三甲基氢氧化铵 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以57%的产率得到2H,3H-环戊二烯并[b]呋喃并[2',3',4':4,5]萘并[2,3-d]呋喃-6-乙酸,8-(3-呋喃基)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-十二氢-3,5-二羟基-2a,5a,6a,7-四甲基-,甲基酯,(2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)-
  参考文献：
  名称：

  印度印za虫的昆虫拒食剂（第5部分）：印za素和一些相关柠檬苦素的化学修饰及其构效关系

  摘要：

  对强效昆虫拒食剂和生长破坏剂印za素（1）以及相关柠檬苦素3-tigloyl印za素（6）和塞兰宁（27）进行化学修饰已使人们能够探索这些化合物的生物活性。人们对拒食效应的结构依赖性作了一般性评论。

  DOI：

  10.1016/s0040-4020(01)81095-4

文献信息

• Structural flexibility in the biocatalyst-mediated functionalization of ring ‘A’ in salannin, a tetranortriterpene from Azadirachta indica
  作者：K. Madhava Madyastha、Krishnamachari Venkatakrishnan

  DOI：10.1039/b004260i

  日期：——

  Nocardia sp. quantitatively converts salannin 1 and 3-de-O-acetylsalannin 2 (C-seco limonoids) into 3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]salannin-1-en-3-one 10, a novel and potentially bioactive compound with an α,β-unsaturated ketone moiety in ring ‘A’. In order to establish the sequence of events involved in this transformation and the structural specificity of this bacterial system, several new derivatives of salannin 1 have been prepared. These studies have indicated that the transformation is initiated by deacetylation at C-3, followed by oxidation of the secondary hydroxy group to 3-keto, which appears to facilitate the elimination of the tigloyloxy/acetoxy group at C-1 with the formation of an olefinic linkage between C-1 and C-2. The organism very efficiently transforms some of the derivatives of salannin into their corresponding compounds possessing an enone system in ring ‘A’, an essential pre-requisite for various biological activities. Some of the C-seco limonoids prepared in the present study, viz. 10, 1,2-didehydro-1,3-dideoxy-3-oxosalannic acid 18, 3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]-20,21,22,23-tetrahydrosalannin-1-en-3-one 15 and 1,2-didehydro-1,3-dideoxy-3-oxosalannol 23 were hitherto not known. p

  诺卡氏菌（Nocardia sp.）能将丹宁1和3-de-O-乙酰基丹宁2（C-seco柠檬酸类）定量转化为3-deacetoxy-1-de[(E)-2-methylbut-2-enoyloxy]salannin-1-en-3-one 10，这是一种新型的、具有潜在生物活性的化合物，其δ,δ²-不饱和酮分子位于环§Aâ。为了确定这种转化所涉及的事件顺序以及这种细菌系统的结构特异性，我们制备了几种丹宁 1 的新衍生物。这些研究表明，这种转化是由 C-3 处的脱乙酰化开始的，随后仲羟基被氧化成 3-酮，这似乎促进了 C-1 处的惕格酰氧基/乙酰氧基的消除，并在 C-1 和 C-2 之间形成了烯烃连接。 该生物体能非常有效地将一些丹宁衍生物转化成相应的化合物，这些化合物在环§Aâ上拥有一个烯酮系统，这是各种生物活性的一个基本前提。本研究中制备的一些C-seco柠檬酸类化合物，即10、1,2-二脱氢-1,3-二脱氧-3-氧代丹宁酸18、3-脱乙酰氧基-1-脱[(E)-2-甲基丁-2-烯酰氧基]-20,21,22,23-四氢丹宁-1-烯-3-酮15和1,2-二脱氢-1,3-二脱氧-3-氧代丹宁醇23，迄今为止尚不为人所知。
• LEY, STEVEN V.;ANDERSON, JAMES C.;BLANEY, WALLY M.;JONES, PHILIP S.;LIDER+, TETRAHEDRON, 45,(1989) N6, C. 5175-5192
  作者：LEY, STEVEN V.、ANDERSON, JAMES C.、BLANEY, WALLY M.、JONES, PHILIP S.、LIDER+

  DOI：——

  日期：——
• ROJATKAR, SUPADA R.;BHAT, VIDYA S.;KULKARNI, MANDAKINI M.;JOSHL, VIMAL S.+, PHYTOCHEMISTRY, 28,(1989) N 1, C. 203-205
  作者：ROJATKAR, SUPADA R.、BHAT, VIDYA S.、KULKARNI, MANDAKINI M.、JOSHL, VIMAL S.+

  DOI：——

  日期：——
• Insect antifeedants from azadirachta indica (part 5): Chemical modification and structure-activity relationships of azadirachtin and some related limonoids
  作者：Steven V. Ley、James C. Anderson、Wally M. Blaney、Philip S. Jones、Zev Lidert、E.David Morgan、Nicholas G. Robinson、Dinos Santafianos、Monique S.J. Simmonds、Peter L. Toogood

  DOI：10.1016/s0040-4020(01)81095-4

  日期：1989.1

  Chemical modification of the potent insect antifeedant and growth-disruption agent azadirachtin (1) and the related limonoids 3-tigloyl azadirachtol (6) and salannin (27) have permitted an exploration of the biological activity of these compounds. General comments are made regarding the structural dependency of the antifeedant effect.

  对强效昆虫拒食剂和生长破坏剂印za素（1）以及相关柠檬苦素3-tigloyl印za素（6）和塞兰宁（27）进行化学修饰已使人们能够探索这些化合物的生物活性。人们对拒食效应的结构依赖性作了一般性评论。