(-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane | 1499182-37-4

• 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
• 英文名称: (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane
• 英文别名: 6β-acetoxyvouacapane；[(4aS,5R,6aS,7R,11aS,11bR)-4,4,7,11b-tetramethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-5-yl] acetate
• CAS: 1499182-37-4
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: RTHBKQKTWBMPLC-LWODCIKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane 在 盐酸 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 26.0h， 生成 (+)-(5S,6R,8S,9S,10S,13R,14R)-6-acetoxy-13-spirocass-Δ¹⁵-en-11-oxo-12,16-olide
  参考文献：
  名称：

  Preparation and Cytotoxic Evaluation of Vouacapane Oxidation Products

  摘要：

  Treatment of (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane (1) with DDQ, mCPBA, or Cr(VI) reagents afforded diterpenoids with various degrees of oxidation at the furan and C rings. Oxidation of 1 using DDQ provided the known benzofuran 2, together with the new derivatives dimer 3, lactone 4, and aldehyde 5, while mCPBA oxidation gave 2, spirocassenolide 6, and cassenolides 7 and 8a. Oxidation of 1 with CrO3 gave 4, 6, 8a, and spirocassenolide 9, while the use of K2Cr2O7 yielded 4, 9, and spirocassenolide 10. The structures of the new compounds followed from HRMS, NMR measurements, and by single-crystal X-ray diffraction of 3, 4, 8b, and 10. Compounds 1, 2, and 6 were evaluated for their cytotoxic activity against the MCF-7 and HL-60 cancer cells, showing moderate cytotoxic activity.

  DOI：

  10.3987/com-19-14195
• 作为产物：
  描述：

  6-oxovoucapane 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.25h， 生成 (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane
  参考文献：
  名称：

  Cassane diterpenes from Caesalpinia platyloba

  摘要：

  The dichloromethane extract from the leaves of Caesalpinia platyloba provided cassane diterpenes whose structures were determined as (-)-(5S,6R,8S,9S,10R,14R)-6-acetoxyvouacapane (1), (-)-(5S,6R,8S,9S, 10R,12Z,14R)-6-acetoxycassa-12,15-diene (3), and (-)-(5S,6R,8S,9S,10R,13E)-6-acetoxycassa-13,15-diene (4). Compound 1 was chemically correlated with (-)-(5S,6R,8S,9S,10R,14R)-6-hydroxyvouacapane (2), (+)-(5S,8S,9S,10R,14R)-6-oxovouacapane (5), and (+)-(5S,6S,8S,9S,10R,14R)-6-acetoxyvouacapane (6), the last one previously isolated from Dipteryx lacunifera. The absolute configurations of all six diterpenes 1-6 were established by comparison of DFT calculated vibrational circular dicroism spectra of 1, 2 and 5 with those obtained experimentally. In addition, several reported chemical shifts for 2 and 5 were reassigned based on two-dimensional NMR measurements. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.028

文献信息

• Epoxy lactones by photooxidative rearrangement of 6β-acetoxyvouacapane
  作者：Armando Talavera-Alemán、Mario A. Gómez-Hurtado、Rosa E. del Río、Jérôme Marrot、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetlet.2017.06.030

  日期：2017.7

  The first study of photooxidation reaction of 6β-acetoxyvouacapane isolated from Caesalpinia platyloba is reported. The reaction yielded four new epoxy lactones, 6β-acetoxy-15,16α-epoxy-13-spirocassa-12,16-olide, 6β-acetoxy-15,16β-epoxy-13-spirocassa-12,16-olide, 6β-acetoxy-12,13β-epoxycassa-16,12-olide and 6β-acetoxy-12,13α-epoxycassa-16,12-olide. All the structures were supported by 1D and 2D NMR

  首次报道了从白Ca中分离得到的6β-乙酰氧基金cap烷的光氧化反应的第一项研究。反应产生了四个新的环氧内酯，6β-乙酰氧基-15,16α-环氧-13-spirocassa-12,16-内酰胺，6β-乙酰氧基-15,16β-环氧-13-spirocassa-12,16-内酰胺，6β-乙酰氧基-12,13β-环氧乙烷-16,12-内酰胺和6β-乙酰氧基-12,13α-环氧乙烷-16,12-内酰胺。所有结构均由1D和2D NMR光谱以及质谱支持。立体化学建立在单晶X射线衍射的基础上。
• Late‐stage functionalization of Vouacapane derivatives from <scp><i>Caesalpinia platyloba</i></scp> by a Groebke−Blackburn−Bienaymé reaction
  作者：Gabriela Servín‐García、Luis Chacón‐García、Alejandro Islas‐Jácome、Mario A. Gómez‐Hurtado、Gabriela Rodríguez‐García、Rosa E. del Río、Carlos J. Cortés‐García

  DOI：10.1002/jhet.4710

  日期：2023.11

  An almost underexplored field within the natural products area is the synthesis of pseudo-natural product libraries by employing isocyanide-based multicomponent reactions as powerful synthetic tools and natural products or their functionalized derivatives as starting reagents. In this work, a novel synthetic strategy behind the late-stage functionalization of fused Vouacapane-azoles in a two-step reaction

  天然产物领域中一个几乎未被充分开发的领域是通过使用基于异氰化物的多组分反应作为强大的合成工具和天然产物或其功能化衍生物作为起始试剂来合成伪天然产物库。在这项工作中，开发了一种在两步反应中对稠合沃阿卡烷唑进行后期功能化的新型合成策略。第一个反应是天然产物 6 β -acetoxyvouacapane 在呋喃环上的 Vilsmeier-Haack 甲酰化反应，该天然产物是从Caesalpinia platyloba叶子的二氯甲烷提取物中分离出来的。第二个反应是 Groebke-Blackburn-Bienaymé 反应，以中等产率合成假天然产物11a-f，其中含有药效基团片段呋喃和咪唑并[1,2- a ]吡啶。这里描述的化合物是生物活性测定的良好候选化合物。