狗牙花碱 E | 117591-81-8

• 物质功能分类: 天然产物 - 萜类
• 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: 狗牙花碱 E
• 中文别名: 狗牙花碱E
• 英文名称: coronarin E
• 英文别名: 3-[(E)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]furan
• CAS: 117591-81-8
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: QXVXYNOIXUIXBI-NDLVVHCESA-N

物化性质

• 熔点：
  94-96 °C(Solv: hexane (110-54-3))
• 沸点：
  359.9±21.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  狗牙花碱 E 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 0.45h， 生成 villosin
  参考文献：
  名称：

  Synthesis of Chinensines A−E

  摘要：

  Short and efficient syntheses of coronarin E (4) and chinensines A-E (5-9) have been accomplished. The use of two different types of reaction of singlet oxygen (O-1(2)) lies at the heart of the synthetic strategy. The syntheses have facilitated the clarification of certain previously unknown, or unconfirmed, stereochemical details (the relativity stereochemistries of chinensines D and E and the absolute stereochemistries for all the synthesized family members).

  DOI：

  10.1021/jo070527v
• 作为产物：
  描述：

  13-表泪杉醇; 13-表迈诺醇 在 2,6-二甲基吡啶 、 potassium permanganate 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氧气 、 magnesium sulfate 、 N-甲基吗啉氧化物 、 苯磺酰氯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.17h， 生成 狗牙花碱 E
  参考文献：
  名称：

  Facile Access to Optically Active Labdane-Type Diterpenes from (+)-Manool. Synthesis of (+)-Coronarin E, (+)-15,16-Epoxy-8(17),13(16),14-labdatriene, and (+)-Labda-8(17),13(Z)-diene-15,16-diol

  摘要：

  An efficient method for the synthesis of (+)-coronarin E (1), (+)-15,16-epoxy-8(17),13(16),14-labdatriene (2), and (+)-labda-8(17),13(Z)-diene-15,16-diol (3) from (+)-manool is described.

  DOI：

  10.1021/np030166o

文献信息

• Synthesis of the marine furanoditerpene (−)-marginatone
  作者：Maria Kolympadi、Maria Liapis、Valentine Ragoussis

  DOI：10.1016/j.tet.2005.01.007

  日期：2005.2

  A synthesis of the marine labdane furanoditerpene (−)-marginatone 1 has been accomplished by a short sequence of reactions starting from (+)-coronarin E 5. The key step is the stereocontrolled-intramolecular electrophilic cyclisation of the (+)-dihydrocoronarin E 6, to the tetracyclic marginatane skeleton 7, which is subsequently functionalized by allylic oxidation to give 1. As (+)-coronarin E 5 was

  海洋拉丹呋喃二萜（-）-marginatone 1的合成已通过从（+）-coronarin E 5开始的短序列反应完成。关键步骤是将（+）-二氢Coronarin E 6立体控制的分子内亲电环化为四环边缘烷烃骨架7，随后通过烯丙基氧化将其官能化，得到1。由于先前从（-）-香紫苏醇10合成了（+）-Coronarin E 5，因此本文报道的制剂构成了（-）-marginatone 1的第一个正式的全合成，已证实其绝对构型。
• Concise Syntheses of Coronarin A, Coronarin E, Austrochaparol and Pacovatinin A
  作者：Takahiro Miyake、Keisuke Uda、Masako Kinoshita、Mikio Fujii、Hiroyuki Akita

  DOI：10.1248/cpb.56.398

  日期：——

  Total syntheses of (+)-coronarin A (1), (+)-coronarin E (2), (+)-austrochaparol (3) and (+)-pacovatinin A (4) were achieved from the synthetic (+)-albicanyl acetate (6). Dess–Martin oxidation of (+)-albicanol (5) derived from the chemoenzymatic product (6) gave an aldehyde (7), which was subjected to Julia one-pot olefination using β-furylmethyl-heteroaromatic sulfones (8 or 9 ) gave (+)-trans coronarin E (2) and (+)-cis coronarin E (12) with high cis-selectivity. The synthesis of (+)-coronarin A (1) from (+)-trans coronarin E (2) was achiev-ed, while (+)-cis coronarin E (12) was converted to the natural products (+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13) and (+)-austrochaparol (3). By the asymmetric synthesis of (+)-3, the absolute structure of (+)-3 was determined to be 5S, 7R, 9R, 10S configurations. Homologation of (+)-albicanol (5) followed by allylic oxidation gave (7α)-hydroxy nitrile (17), which was finally converted to the natural (+)-pacovatinin A (4) in 8 steps from (+)-albicanol (5).

  从合成产物(+)-albicanyl acetate (6)中获得了(+)-coronarin A (1)、(+)-coronarin E (2)、(+)-austrochaparol (3)和(+)-pacovatinin A (4)的完全合成。(+)-albicanol (5)的Dess-Martin氧化反应来自化学酶产物(6)，生成醛(7)，后者与β-呋喃甲基杂芳砜(8或9)进行Julia一锅法烯化反应，得到具有高顺式选择性的(+)-反式coronarin E (2)和(+)-顺式coronarin E (12)。从(+)-反式coronarin E (2)中获得了(+)-coronarin A (1)的合成，而(+)-顺式coronarin E (12)则转化为天然产物(+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13)和(+)-austrochaparol (3)。通过(+)-3的不对称合成，确定(+)-3的绝对结构为5S,7R,9R,10S构型。(+)-albicanol (5)的同分异构化反应后，发生烯丙基氧化反应，生成(7α)-
• Lewis Acid‐Catalyzed Stereoselective α‐Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides
  作者：Anna Adamkiewicz、Izabela Węglarz、Aleksandra Butkiewicz、Marta Woyciechowska、Jacek Mlynarski

  DOI：10.1002/adsc.201901218

  日期：2020.2.6

  stereoselective α‐addition to cyclic dienol silanes has rarely been exploited, in contrast to the well‐studied γ‐addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α‐addition of 2‐trimetylsiloxy furan to optically pure aldehydes in water‐containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural

  与对丁二酸内酯共轭的γ-加成研究相比，对环二烯醇硅烷的立体选择性α-加成很少被利用。在这项研究中，报道了在含水溶剂中空前催化2-三甲硅氧基甲氧基呋喃的Mukaiyama aldolα-加成到光学纯醛中的现象。该概念的合成效用在六种生物活性天然产物的有效合成中得到了证明：维特索利德D，姜黄素肌醇C，短毛菌素，海胆碱C，（+）- Coronarin E和（E）-labda‐7,11,13‐trien‐ 16,15-橄榄。
• A concise synthesis and in vitro cytotoxicity of new labdane diterpenes
  作者：Mankil Jung、Imju Ko、Seokjoon Lee、Sun Ju Choi、Byoung Hee Youn、Soo Kie Kim

  DOI：10.1016/s0960-894x(98)00603-9

  日期：1998.12

  A new series of labdane-related diterpenes have been synthesized from (-)-sclareol and assayed in vitro cytotoxicity against mouse and human cancer cells. A key intermediate, homodrimane and furanolabdane derivatives show good in vitro cytotoxicity comparable to those of mitomycin C and adriamycin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of (+)-coronarin E
  作者：Martin Müller、Jörg Schröder、Christine Magg、Karlheinz Seifert

  DOI：10.1016/s0040-4039(98)00861-2

  日期：1998.6

  The labdane-type diterpenoid (+)-coronarin E (5) has been synthesized in 7 steps from (-)-sclareol (1) for the first time. (C) 1998 Elsevier Science Ltd. All rights reserved.