ent-13-epi-8,13-epoxy-2,3-secolabd-14-ene-2,3-dioic acid dimethyl ester | 215030-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ent-13-epi-8,13-epoxy-2,3-secolabd-14-ene-2,3-dioic acid dimethyl ester
• 英文别名: ent-13-epi-8,13-epoxy-2,3-secolabd-14-en-2,3-oic acid dimethyl ester；methyl 2-[(2R,4aS,5R,6S,8aS)-2-ethenyl-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydrochromen-6-yl]-2-methylpropanoate
• CAS: 215030-25-4
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: OACQCWZSSHUJFU-PEYIGDRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ent-13-epi-8,13-epoxy-2,3-secolabd-14-ene-2,3-dioic acid dimethyl ester 在 四氧化锇 、 双氧水 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以50%的产率得到2-[(2R,4aS,5R,6S,8aS)-2-((S)-1,2-Dihydroxy-ethyl)-5-methoxycarbonylmethyl-2,5,8a-trimethyl-octahydro-chromen-6-yl]-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  New Bis-secolabdane Diterpenoids from Excoecaria agallocha

  摘要：

  Two new bis-secolabdane diterpenoids, excoecarins R1 (1) and R2 (2), were isolated from the resinous wood of Excoecaria agallocha. The structures of I and 2 were established on the basis of spectroscopic data interpretation and chemical evidence.

  DOI：

  10.1021/np020321j
• 作为产物：
  描述：

  ent-13-epi-8,13-epoxy-2-hydroxylabda-1,14-dien-3-one 在 甲醇 、 氢氧化钾 、 双氧水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 27.0h， 生成 ent-13-epi-8,13-epoxy-2,3-secolabd-14-ene-2,3-dioic acid dimethyl ester
  参考文献：
  名称：

  Five New Labdane-Type Diterpenes from Excoecaria agallocha. IV.

  摘要：

  从印度楝树脂木中分离出五种新的腊烷型二萜。这些化合物的结构被确定为ent-13-epi-8, 13-epoxy-2-hydroxylabda-1, 14-dien-3-one (1)、ent-13-epi-8, 13-epoxy-14S, 15-dohydroxylabdan-3-one (2)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid (3)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid 3-methyl ester (4)和ent-13-epi-8, 13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid (5)。

  DOI：

  10.1248/cpb.46.1393

文献信息

• Stereostructures of New Labdane-Type Diterpenes, Excoecarins F, G1, and G2 from the Wood of Excoecaria agallocha.
  作者：Tenji KONISHI、Takao KONOSHIMA、Yasuhiro FUJIWARA、Shiu KIYOSAWA、Kazumoto MIYAHARA、Masatoshi NISHI

  DOI：10.1248/cpb.47.456

  日期：——

  Three new labdane-type diterpenes, excoecarins F, G1, and G2, were isolated from resinous wood of Excoecaria agallocha LINN collected from Okinawa prefecture. Stereochemistries of the new diterpenes were determined on the basis of chemical and physicochemical evidence. Excoecarin F was found to posses a chloride element in its structure.

  从冲绳县采集的槟榔科植物槟榔的树脂木中分离出三种新的腊烷型二萜类化合物，即槟榔素F、G1和G2。根据化学和物理化学证据确定了新二萜类化合物的立体化学结构。槟榔素F的结构中存在氯元素。
• Five New Labdane-Type Diterpenes from Excoecaria agallocha. IV.
  作者：Tenji KONISHI、Yasuhiro FUJIWARA、Takao KONOSHIMA、Shiu KIYOSAWA

  DOI：10.1248/cpb.46.1393

  日期：——

  Five new labdane-type diterpenes were isolated from the resinous wood of Excoecaria agallocha. The structures of these compounds were established as ent-13-epi-8, 13-epoxy-2-hydroxylabda-1, 14-dien-3-one (1), ent-13-epi-8, 13-epoxy-14S, 15-dohydroxylabdan-3-one (2), ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid (3), ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid 3-methyl ester (4) and ent-13-epi-8, 13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid (5).

  从印度楝树脂木中分离出五种新的腊烷型二萜。这些化合物的结构被确定为ent-13-epi-8, 13-epoxy-2-hydroxylabda-1, 14-dien-3-one (1)、ent-13-epi-8, 13-epoxy-14S, 15-dohydroxylabdan-3-one (2)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid (3)、ent-13-epi-8, 13-epoxy-2, 3-secolabd-14-ene-2, 3-dioic acid 3-methyl ester (4)和ent-13-epi-8, 13-epoxy-2-oxa-3-oxolabd-14-ene-1R-carboxylic acid (5)。
• New Bis-secolabdane Diterpenoids from <i>Excoecaria agallocha</i>
  作者：Tenji Konishi、Kiyonori Yamazoe、Takao Konoshima、Takashi Maoka、Yasuhiro Fujiwara、Kazumoto Miyahara

  DOI：10.1021/np020321j

  日期：2003.1.1

  Two new bis-secolabdane diterpenoids, excoecarins R1 (1) and R2 (2), were isolated from the resinous wood of Excoecaria agallocha. The structures of I and 2 were established on the basis of spectroscopic data interpretation and chemical evidence.