(1R,5S)-6-oxabicyclo[3.2.1]octan-7-one | 4350-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5S)-6-oxabicyclo[3.2.1]octan-7-one
• 英文别名: cis-3-Hydroxy-cyclohexan-carbonsaeure-(1)-lacton；cis-3-Hydroxy-cyclohexan-carbonsaeure-lacton；1,3-Cyclohexencarbolacton；6-Oxa-bicyclo[3.2.1]octan-7-one
• CAS: 4350-83-8
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: KKVBULDFFNFYHJ-RITPCOANSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  254.8±8.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  (1R,5S)-6-oxabicyclo[3.2.1]octan-7-one 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 C₇H₁₂O₂
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  Leustroducsin B was synthesized via a convergent route based on division of the leustroducsin molecule into three segments A, B, and C. Two coupling reactions (Julia coupling reaction and Nozaki-Hiyama-Kishi (NHK) reaction) were employed for coupling of segments A and 13: segment A, for the Julia coupling reaction was prepared by a combination of Sharpless asymmetric epoxidation and an epoxide-cleavage reaction with an organoaluminum reagent, while segment A, for the NHK reaction was synthesized from optically active alcohol that had previously been prepared by lipase-catalyzed kinetic resolution. Segment B, whose structure was modified with some functional groups, was synthesized from (R)-malic acid by a combination of Wittig reaction and Sharpless asymmetric dihydroxylation, and segment C, containing a cyclohexane moiety, was prepared by asymmetric Diels-Alder reaction. Segment B was first coupled with segment A, via the Julia coupling reaction, but the yield was low due to unexpected epimerization. The NHK reaction of segment A2 proceeded to give the coupling product in good yield. This product was coupled with segment C via Wittig and Stille coupling reactions, and finally, phosphorylation was carried out by partial hydrolysis of a cyclic phosphate to give leustroducsin B.

  DOI：

  10.1021/jo8005599
• 作为产物：
  描述：

  (R)-3-环己烯甲酸 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 碘 、 碳酸氢钠 、 potassium iodide 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 27.0h， 生成 (1R,5S)-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  融合途径合成全亮氨酸B

  摘要：

  通过一种聚合途径实现了总的合成过程，其中包括段A与段B的Julia偶联反应以及段C的Stille偶联反应。

  DOI：

  10.1016/j.tetlet.2007.03.152

文献信息

• METHOD FOR THE PREPARATION OF ENANTIOMER FORMS OF CIS-CONFIGURED 3-HYDROXYCYCLOHEXANE CARBOXYLIC ACID DERIVATIVES USING HYDROLASES
  申请人：Holla Wolfgang

  公开号：US20070197788A1

  公开（公告）日：2007-08-23

  The present invention relates to a process for preparing chiral non-racemic cis-configured cyclohexanols or cyclohexanol derivatives of the formula (I) Cis-configured hydroxyl-cyclohexane carboxylic acid derivatives of formula (I) are central building blocks or immediate precursors for the medicinally active compounds which allow a therapeutic modulation of the lipid and/or carbohydrate metabolism and are thus suitable for preventing and/or treating type II diabetes, hyperglycemia and artherosclerosis. The cis-configured hydroxyl-cyclohexane carboxylic acid derivatives of formula (I) are central building blocks or immediate precursors for the medicinally active compounds described in the prior art.

  本发明涉及一种制备手性非外消旋顺式环己醇或环己醇衍生物的过程，其化学式为(I)。化学式(I)的顺式羟基环己烷羧酸衍生物是中心构建块或药物活性化合物的直接前体，可用于治疗脂质和/或碳水化合物代谢，因此适用于预防和/或治疗II型糖尿病、高血糖和动脉硬化。化学式(I)的顺式羟基环己烷羧酸衍生物是先前技术中描述的药物活性化合物的中心构建块或直接前体。
• Re₂O₇/HReO₄ Mediated Intramolecular Hydroacyloxylation of Unactivated Alkenes: A Dual Hydrogen-Bonding Effect
  作者：Yibing Liu、Liqun Hu、Yuzhu Zheng、Xiong Fang、Youwei Xie

  DOI：10.1021/acs.orglett.2c03846

  日期：2023.1.13

  challenging intramolecular hydroacyloxylation reaction. Both HFIP and an internal carboxy group have been proven to be crucial for the successful implementation of this transformation; these are proposed to assist the formation and stabilization of the key cationic intermediate via hydrogen-bonding interactions with perrhenate anion (ReO4–).

  该出版物描述了 Re 2 O 7在六氟异丙醇 (HFIP) 中的应用，用于活化惰性和电子失活的烯烃，以促进具有挑战性的分子内加氢酰氧基化反应。HFIP 和内部羧基均已被证明对于成功实施这一转变至关重要；这些被提议通过与高铼酸盐阴离子 (ReO 4 – )的氢键相互作用来帮助关键阳离子中间体的形成和稳定。
• Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and Secondary <i>γ</i>-C–H Bonds
  作者：Arnau Call、Giorgio Capocasa、Andrea Palone、Laia Vicens、Eric Aparicio、Najoua Choukairi Afailal、Nikos Siakavaras、Maria Eugènia López Saló、Massimo Bietti、Miquel Costas

  DOI：10.1021/jacs.3c06231

  日期：2023.8.16

  Chiral oxygenated aliphatic moieties are recurrent in biological and pharmaceutically relevant molecules and constitute one of the most versatile types of functionalities for further elaboration. Herein we report a protocol for straightforward and general access to chiral γ-lactones via enantioselective oxidation of strong nonactivated primary and secondary C(sp3)–H bonds in readily available carboxylic

  手性氧化脂肪族部分在生物和药物相关分子中反复出现，并构成了需要进一步阐述的最通用的功能类型之一。在此，我们报告了一种通过对易获得的羧酸中的强非活化伯键和仲 C( sp 3 )–H 键的对映选择性氧化来直接和一般地获得手性γ -内酯的方案。关键的实现方面是使用强大的空间阻碍锰催化剂，使用过氧化氢作为氧化剂提供出色的对映选择性（高达 >99.9%）和产率（高达 96%）。所得的γ-内酯对于天然产物和可回收聚合物材料的制备具有直接意义。
• ANTIARRHYTHMIC DRUG, ATRIAL FIBRILLATION INHIBITOR, MODEL OF SUSTAINED ATRIAL FIBRILLATION AND METHOD FOR PRODUCING SAME, AND METHOD FOR SCREENING ATRIAL FIBRILLATION INHIBITOR
  申请人：Toho University

  公开号：EP2702990A1

  公开（公告）日：2014-03-05

  An atrial fibrillation inhibitor, including: a compound expressed by one of the following Structural Formulas (I) to (VI) or a pharmacologically acceptable salt thereof, wherein the atrial fibrillation inhibitor inhibits atrial fibrillation: where in the Structural Formula (III), Gluc refers to glucuronic acid.

  一种心房颤动抑制剂，包括：由以下结构式（I）至（VI）之一表示的化合物或其药理学上可接受的盐，其中心房颤动抑制剂可抑制心房颤动： 其中结构式（III）中，Gluc 指葡萄糖醛酸。
• Heterolytic fragmentation of 1,3-dithianyl tosylates
  作者：James A. Marshall、John L. Belletire

  DOI：10.1016/s0040-4039(01)96577-3

  日期：1971.1