2-oxa-cis-bicyclo<3.3.0>octane-3-one-6-exo-carbaldehyde

• 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: 2-oxa-cis-bicyclo<3.3.0>octane-3-one-6-exo-carbaldehyde
• 英文别名: γ-lactone of 5α-hydroxy-2β-formyl-1α-cyclopentaneacetic acid；(+/-)-3-oxo-2-oxa-cis-bicyclo<3.3.0>octane-6-exo-carbaldehyde；(3aR*,4S*,6aS*)-2-Oxo-3,3a,4,6a-tetrahydro-2H-cyclopentafuran-4-carbaldehyde；(1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one；(3aR,4S,6aS)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: DOBNBRNXWCUUQW-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxa-cis-bicyclo<3.3.0>octane-3-one-6-exo-carbaldehyde 生成 (1S,5R,6R)-6-[(E)-(4RS)-4-Methyl-3-oxo-1-octen-6-ynyl]-2-oxabicyclo[3,3,0]octan-3-one
  参考文献：
  名称：

  Novel acetylenic prostaglandins and processes for the preparation thereof

  摘要：

  Prostane衍生物的化学式为##STR1##其中R.sub.1是残基OR.sub.2，R.sub.2是氢，烷基，环烷基，芳基或杂环残基；或者是NHR.sub.3，其中R.sub.3是由最多15个碳原子的烃羧酸或磺酸衍生的酰基；A是--CH.sub.2 --CH.sub.2 --或顺式--CH.dbd.CH-- Z是酰基或##STR2##其中OR.sub.4基团可以在α-或β-位置，R.sub.4是H或羟基保护基团XY是##STR3##其中R.sub.4如上定义，--CH.sub.2 --CH.sub.2 --或--CH.sub.2 --CH--其中R.sub.5是烷基或1-5个碳原子，如果Z是R.sub.5酰基或##STR4##当Z是酰基时，X Y代表--CH.dbd.CH--：R.sub.6，R.sub.7，R.sub.8，R.sub.9和R.sub.10各自独立地是氢或1-5个碳原子的烷基；R.sub.11是1-5个碳原子的烷基；如果R.sub.2是氢，则其与生理兼容碱盐具有延长活性持续时间和增加有效性选择性的前列腺素。

  公开号：

  US04235930A1
• 作为产物：
  描述：

  (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde 在 palladium on activated charcoal 1,5-二氮杂双环[4.3.0]壬-5-烯 、 氢气 作用下， 生成 2-oxa-cis-bicyclo<3.3.0>octane-3-one-6-exo-carbaldehyde
  参考文献：
  名称：

  Buzzetti, Franco; Faustini, Franco; Orzi, Fabrizio, Gazzetta Chimica Italiana, 1985, vol. 115, # 7, p. 351 - 356

  摘要：

  DOI：

文献信息

• An Approach to the Tricyclic Lactone Core of Brasoside and Related Natural Products
  作者：Jeremy Robertson、Morgan Ménard、Rhonan Ford

  DOI：10.1055/s-2004-835637

  日期：——

  A one-pot iodine atom transfer/cyclisation and inter­molecular olefination is described for the efficient, stereoselective construction of bicyclic lactone intermediates en route to compound 21, a potential precursor to the brasoside (1) skeleton.

  描述了一种单锅碘原子转移/环化和分子间烯烃化的方法，用于高效、立体选择性地构建双环内酯中间体，作为合成复合物21的途径，这是一种潜在的brasoside (1) 骨架前体。
• Conversion of (-)-limonen-10-ol to 11-deoxyprostaglandin.
  作者：HIROSHI SUEMUNE、HIROSHI MARUOKA、SEITARO SAEKI、KIYOSHI SAKAI

  DOI：10.1248/cpb.34.4629

  日期：——

  This paper describes a conversion of (-)-limonen-10-ol to the key intermediate (1) for 11-deoxyprostaglandin. The 3, 4-cis-disubstituted cyclopentanone (2), which was easily obtained from (-)-limonen-10-ol in a stereocontrolled fashion by means of Rh(I)-catalyzed cyclization via the 4-pentenal derivative, could be directly converted to the bicyclo[3.3.0]octenone (3) by treatment with KHSO4 in boiling benzene. Compound 3 with a double bond at the favorable position was converted to 1 by way of fission of the double bond and subsequent modification of substituents on the five-membered ring.

  本文介绍了 (-)-limonen-10-ol 转化为 11-脱氧前列腺素关键中间体 (1) 的过程。通过 Rh(I)-catalyzed cyclization via the 4-pentenal derivative，以立体可控的方式从 (-)-limonen-10-ol 轻松获得 3，4-顺式二取代环戊酮 (2)，在沸腾的苯中通过 KHSO4 处理，可直接转化为双环[3.3.0]辛烯酮 (3)。化合物 3 的有利位置上有一个双键，通过双键裂解和随后对五元环上的取代基进行修饰，可转化为 1。
• NOVEL PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND INTERMEDIATES THEREOF
  申请人：Aswathanarayanappa Chandrashekar

  公开号：US20120209011A1

  公开（公告）日：2012-08-16

  This invention relates to novel process for the preparation of prostaglandin compounds having formula (K), wherein R is selected from the group consisting of C 1 -C 7 alkyl; C 7 -C 17 aralkyl wherein the aryl group is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkyl, halo and CF 3 ; and (CH 2 ) n OR 2 wherein n is from 1 to 3 and R 2 represents a C 6 -C 10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C 1 -C 6 alkyl, halo and CF 3 ; and R 1 is selected from OR 3 and NHR 3 wherein R 3 is C 1 -C 6 alkyl, H; and dashed lines represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.

  本发明涉及一种新型的制备具有式（K）的前列腺素化合物的方法，其中R选自以下组中的一种：C1-C7烷基；C7-C17芳基烷基，其中芳基基团未取代或取代有1至3个取代基，所述取代基选自C1-C6烷基，卤素和CF3；以及（CH2）nOR2，其中n为1至3，R2代表未取代或取代有1至3个取代基的C6-C10芳基基团，所述取代基选自C1-C6烷基，卤素和CF3；R1选自OR3和NHR3，其中R3为C1-C6烷基，H；虚线表示双键或单键。本发明还公开了新型中间体。
• Process for the preparation of oxaprostaglandin intermediates
  申请人：Schering Aktiengesellschaft

  公开号：US04191823A1

  公开（公告）日：1980-03-04

  In a process for the preparation of an oxaprostaglandin intermediate of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl, or a free or functionally modified hydroxy group; R.sub.2 and R.sub.3 are the same or different, and each is hydrogen, halogen or alkyl; R.sub.4 is alkyl or optionally substituted aryl; and n is 0, 1, 2 or 3; which comprises reacting an aldehyde of the formula ##STR2## wherein R.sub.1 is as defined above with an anion of the formula ##STR3## wherein n, R.sub.2, R.sub.3 and R.sub.4 are as defined above; and R.sub.5 is alkyl; an improvement is provided wherein the anion is added to the reaction medium in a form which consists essentially of its crystalline alkali metal salt of the formula ##STR4## wherein A is an alkali metal atom.

  本发明涉及一种制备氧前列素中间体的方法，该中间体的化学式为##STR1##其中R.sub.1是氢，烷基或自由或功能修饰的羟基；R.sub.2和R.sub.3相同或不同，每个是氢，卤素或烷基；R.sub.4是烷基或可选择的取代芳基；n为0，1，2或3；包括将化学式为##STR2##其中R.sub.1如上定义的醛与化学式为##STR3##其中n，R.sub.2，R.sub.3和R.sub.4如上定义的阴离子反应；R.sub.5是烷基；提供了一种改进，其中阴离子以其结晶的碱金属盐的形式加入到反应介质中，该碱金属盐的化学式为##STR4##其中A是碱金属原子。
• Tolstikov, G. A.; Miftakhov, M. S.; Akbutina, F. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 268 - 277
  作者：Tolstikov, G. A.、Miftakhov, M. S.、Akbutina, F. A.

  DOI：——

  日期：——