9,10-bis(hydroxymethyl)tricyclo[4.2.2.0^2,5]deca-3,7-diene | 56711-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9,10-bis(hydroxymethyl)tricyclo[4.2.2.0^2,5]deca-3,7-diene
• 英文别名: cis-7,8-bis(hydroxymethyl)-anti-tricyclo[4.2.2.0^2,5]deca-3,9-diene；7,8-Di-hydroxymethyl-tricyclo<4,2,2,0^2,5>decadien(3,9)(endo-cis-anti)；[(1R,2R,5S,6S,7S,8R)-8-(hydroxymethyl)-7-tricyclo[4.2.2.02,5]deca-3,9-dienyl]methanol
• CAS: 56711-59-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BBCVWBYIGLSLER-CJXDBHJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  9,10-bis(hydroxymethyl)tricyclo[4.2.2.0^2,5]deca-3,7-diene 在 臭氧 、 二甲基硫 、 amberlyst-15 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以40%的产率得到perhydro-2,3,4,5,6-pentaoxacyclopenta[ij]pentaleno[2,1,6,5-cdef]s-indacene
  参考文献：
  名称：

  Oxa Bowls:  Studies Toward Hexaoxa-[6]-peristylane. Synthesis of a Seco-Derivative of Hexaoxa-[6]-peristylane

  摘要：

  When the concept of equivalency of all-cis-[n]-formyl-[n]-cycloalkanes with [n]-oxa-[n]-peristylanes was followed, an approach to the "oxa bowl" hexaoxa-[6]-peristylane 4a was delineated. This required an access to all-cis-cyclohexane-hexacarbaldehyde 5, which could be subjected to a 6-fold intramolecular acetalization cascade. A readily available Diels-Alder adduct of cyclooctatetraene and maleic anhydride was chosen as the starting material and was elaborated to the endo, endo-tetraene 6 in which all the six aldehyde functionalities are present in a latent form with cis orientation in a locked cyclohexane ring. Although ozonolysis of 6 has so far led only to intractable products, the novelty and brevity of our approach have been demonstrated through the intramolecular acetalizations through ozonolysis in 7 and 15, leading to oxa bowls 9 (seco-hexaoxaperistylane) and 16, respectively. The formation of 9 and 16 requires the generation of five tetrahydrofuran and four oxacyclic rings, respectively, in a single-pot operation.

  DOI：

  10.1021/jo010223n
• 作为产物：
  描述：

  endo-tricyclo<4.2.2.0^2,5>deca-3,9-diene-7,8-dicarboxylate anhydride 在 lithium aluminium tetrahydride 作用下， 生成 9,10-bis(hydroxymethyl)tricyclo[4.2.2.0^2,5]deca-3,7-diene
  参考文献：
  名称：

  Silver(I) ion catalyzed rearrangements of strained .sigma. bonds. XXIX. Influence of structural features on the course of transition metal catalyzed 1,8-bishomocubane rearrangements

  摘要：

  DOI：

  10.1021/ja00838a026

文献信息

• CpRuCl(PPh₃)₂-Catalyzed Cyclopropanation of Bicyclic Alkenes with Tertiary Propargylic Acetates
  作者：Alphonse Tenaglia、Sylvain Marc

  DOI：10.1021/jo060276a

  日期：2006.4.1

  The electron-rich cyclopentadienylruthenium complex CpRuCl(PPh3)2 turns out to be an efficient catalyst for the regio- and stereoselective cyclopropanation of bicyclic alkenes with tertiary propargylic carboxylates. The reaction provides 1,2,3-trisubstituted cyclopropanes in high yields as a single stereoisomer instead of the expected cyclobutenes via [2 + 2] cycloaddition. Functional groups such as

  富电子的环戊二烯基钌络合物CpRuCl（PPh 3）2证明是具有叔炔丙基羧酸酯的双环烯烃的区域和立体选择性环丙烷化的有效催化剂。该反应以单一立体异构体的形式高收率地提供1,2,3-三取代的环丙烷，而不是通过[2 + 2]环加成反应生成的预期环丁烯。催化反应可耐受诸如醚，酯，醇，酚，酮，酯，羧酸酐，腈，卤化物，砜，酰亚胺，氨基甲酸酯和嗪等官能团。还证明了有效的环丁烯环丙烷化，提供了紧张的双环[2.1.0 1,3 ]戊烷骨架。
• Polymer Self-Assembly into Unique Fractal Nanostructures in Solution by a One-Shot Synthetic Procedure
  作者：Suyong Shin、Ming-Long Gu、Chin-Yang Yu、Jongseol Jeon、Eunji Lee、Tae-Lim Choi

  DOI：10.1021/jacs.7b11630

  日期：2018.1.10

  spontaneously underwent self-assembly during polymerization by an in situ nanoparticlization of conjugated polymers (INCP) method. The formation of fractal structures in solution was confirmed by various imaging techniques such as atomic force microscopy, transmission electron microscopy (TEM), and cryogenic TEM. The diffusion-limited aggregation theory was adopted to explain the branching patterns

  具有高表面积的分形纳米结构可能在传感器、催化剂、功能涂层以及生物医学和电子应用中有用。已经报道了使用各种无机或有机化合物在固体基材上制备分形纳米结构。然而，使用溶液中的聚合物来实现这样的过程极具挑战性。在这里，我们报告了通过由聚合和自组装动力学控制的前所未有的组装机制在溶液中简单地一次性制备聚合物分形纳米结构。这是可能的，因为一种单体的反应性明显高于另一种，从而容易形成二嵌段共聚物的微观结构。然后，通过共轭聚合物的原位纳米颗粒化（INCP）方法，含有聚（对亚苯基亚乙烯基）（PPV）而没有任何侧链的第二个不溶性嵌段在聚合过程中自发地经历了自组装。溶液中分形结构的形成已通过原子力显微镜、透射电子显微镜 (TEM) 和低温 TEM 等各种成像技术得到证实。根据聚合条件的变化，如单体浓度和添加剂的存在，采用扩散限制聚集理论来解释分形纳米结构的支化模式。最后，经过详细的动力学分析，我们提出了形成独特分形纳米结构的合理机制，
• Living Alternating Ring‐Opening Metathesis Copolymerization of 2,3‐Dihydrofuran to Provide Completely Degradable Polymers
  作者：Taeyang An、Hanseul Ryu、Tae‐Lim Choi

  DOI：10.1002/anie.202309632

  日期：2023.11.20

  We report the DHF copolymers with enhanced alternating ratios and degradability. By carefully tuning the ROMP reactivities of comonomers and Ru initiators, we achieved an outstanding A, B-alternation (up to 98 %), while preserving the benefits of living polymerization. The superior degradability of our copolymers was also demonstrated by the notable NMR yield of the unimeric degradation products (up

  我们报道了具有增强交替比和可降解性的 DHF 共聚物。通过仔细调整共聚单体和 Ru 引发剂的 ROMP 反应活性，我们实现了出色的 A、B 交替（高达 98%），同时保留了活性聚合的优势。我们的共聚物具有出色的降解性，这一点还通过单聚降解产物的显着 NMR 收率（高达 80%）和回收率（66% 收率）得到了证明。
• Rao, H. Surya Prakash; Senthilkumar; Reddy, D. Srinivasa, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 260 - 263
  作者：Rao, H. Surya Prakash、Senthilkumar、Reddy, D. Srinivasa、Mehta, Goverdhan

  DOI：——

  日期：——
• Stereochemistry and mechanism of electrophilic additions to tricyclo[4.2.2.02,5]deca-3,7-diene derivatives
  作者：Goverdhan Mehta、Paras N. Pandey

  DOI：10.1021/jo00913a002

  日期：1975.12