(4R,6R)-5,5-dimethylnona-1,8-diene-4,6-diol | 864514-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,6R)-5,5-dimethylnona-1,8-diene-4,6-diol
• CAS: 864514-24-9
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: QLRPWSGFPOVURF-NXEZZACHSA-N

物化性质

• 沸点：
  285.4±40.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,6R)-5,5-dimethylnona-1,8-diene-4,6-diol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 二氯苯酚溴酯 、 四丁基氟化铵 、 氢气 、 titanium(IV)isopropoxide 、 戴斯-马丁氧化剂 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 臭氧 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 zinc(II) iodide 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 69.34h， 生成 irciniastatin A
  参考文献：
  名称：

  Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs

  摘要：

  Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, similar to 14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (similar to 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.

  DOI：

  10.1021/ja3057612
• 作为产物：
  描述：

  乙酸烯丙酯 、 2,2-二甲基-1,3-丙二醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 caesium carbonate 、 4-氯-3-硝基苯甲酸 、 (S)-(-)-5,5-二氯-6,6-二甲氧基-2,2-双(二苯基磷酸)-1,1-联苯基 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.5h， 以48%的产率得到(4R,6R)-5,5-dimethylnona-1,8-diene-4,6-diol
  参考文献：
  名称：

  Lu, Yu; Kim, In Su; Hassan, Abbas, Angewandte Chemie - International Edition, 2009, vol. 48, p. 5018 - 5021

  摘要：

  DOI：

文献信息

• Synthesis and Complete Stereochemical Assignment of Psymberin/Irciniastatin A
  作者：Xin Jiang、Jorge García-Fortanet、Jef K. De Brabander

  DOI：10.1021/ja0537068

  日期：2005.8.1

  We describe a concise and flexible synthetic avenue for the preparation of compounds with structures relevant to those proposed for the novel marine-derived differential cytotoxins psymberin and irciniastatin A. Our efforts led to their complete stereochemical assignment and the notion that psymberin and irciniastatin A are identical compounds. Our total synthesis features an interesting termini-differentiating

  我们描述了一种简洁灵活的合成途径，用于制备结构与新型海洋衍生差异细胞毒素 psymberin 和 irciniastatin A 相关的化合物。我们的努力导致了它们的完整立体化学分配以及 psymberin 和 irciniastatin A 相同的概念化合物。我们的全合成具有从 C2 对称双烯烃前体获得的二醛的有趣的末端差异化乳醇化、差向异构腈的温和铂催化水解、制备灵敏的亚胺酸甲酯的新方案和一锅法转化这些亚胺酯转化为 N-酰基胺。从片段 5-7 开始（每个片段准备 7-8 个步骤，
• Conformational Analysis ofoligo-1,3-Dioxanylmethanes
  作者：Thomas Trieselmann、Reinhard W. Hoffmann、Karsten Menzel

  DOI：10.1002/1099-0690(200204)2002:7<1292::aid-ejoc1292>3.0.co;2-6

  日期：2002.4

  Stereoselective synthesis of a series of 1,3-dioxan-4-ylmethanes 1−9 has been achieved by use of solely substrate-based asymmetric induction. The simple C2-symmetric bis(dioxanyl)methane 1 has a greater than 99% conformational preference at the two inter-ring bonds for the conformation 1a. The homologous structures 3−9 contain up to five dioxanylmethane units, maintaining a high conformational preference

  一系列 1,3-二恶烷-4-基甲烷 1-9 的立体选择性合成已通过仅使用基于底物的不对称诱导实现。简单的 C2 对称双（二氧杂环己基）甲烷 1 在构象 1a 的两个环间键处具有大于 99% 的构象偏好。同源结构 3-9 包含多达五个二恶烷基甲烷单元，在每个双（二恶烷基）甲烷单元中保持高构象偏好。因此，这些柔性化合物在多达八个可旋转的环间键上达到超过 90% 的构象偏好。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Synthesis and complete stereochemical assignment of psymberin/irciniastatin for use as antitumor compounds
  申请人：Brabander De Jef

  公开号：US20070015821A1

  公开（公告）日：2007-01-18

  The invention relates to the synthesis and complete stereochemical assignments of cytotoxic compounds such as compound 28-a and its stereoisomers: The invention further provides processes for making the compounds, their synthetic intermediates, and for methods of using the compounds and their pharmaceutical compositions for the treatment of neoplastic diseases.

  该发明涉及合成和对细胞毒性化合物的完全立体化学赋值，如化合物28-a及其立体异构体。该发明还提供了制备这些化合物、它们的合成中间体的方法，以及使用这些化合物及其药物组合物治疗肿瘤性疾病的方法。
• Synthesis of Psymberin Analogues:  Probing a Functional Correlation with the Pederin/Mycalamide Family of Natural Products
  作者：Xin Jiang、Noelle Williams、Jef K. De Brabander

  DOI：10.1021/ol062656o

  日期：2007.1.1

  In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results

  在这封信中，我们描述了“ psympederin”的有效合成方法，“ psympederin”是新型抗肿瘤天然产物psymberin与水泡甲虫毒素pederin的混合物。对抗增殖活性的评估表明，二氢异香豆素片段对于Psymberin毒性很重要，而环状有花药片段对pederin / mycalamide毒性很重要。根据本文所述的初步结果，我们推测，尽管它们在结构上相似，但psymberin和pederin / mycalamide通过不同的机制诱导毒性。[反应：请参见文字]。
• US7429616B2
  申请人：——

  公开号：US7429616B2

  公开（公告）日：2008-09-30