rosaprostol | 56695-65-9

• 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: rosaprostol
• 英文别名: 7-[(1S,2R)-2-hexyl-5-hydroxycyclopentyl]heptanoic acid
• CAS: 56695-65-9
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: NMAOJFAMEOVURT-GARXDOFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  乙醇 、 rosaprostol 在 硫酸 作用下， 生成 19,20-Di-nor-9-hydroxy-prostan-saeure-aethylester
  参考文献：
  名称：

  Valcavi; Innocenti; Zabban, Farmaco, Edizione Scientifica, 1975, vol. 30, # 7, p. 527 - 535

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-Methyl 2-hexyl-5-oxocyclopentaneheptanoate 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 rosaprostol
  参考文献：
  名称：

  A New Synthesis of Racemic Rosaprostol

  摘要：

  从 3-（二甲氧基磷酰甲基）环戊-2-烯酮（6）开始，通过五个步骤制备了抗溃疡药物罗沙前列醇，总收率为 36%。6 与 7-iodo heptanoate 甲酯在 C(2)处发生的区域选择性烷基化反应，以及随后与戊醛发生的 Horner-Wittig 反应，构成了整个合成过程的关键步骤。

  DOI：

  10.1055/s-2000-6316

文献信息

• Electroreductive intramolecular coupling of γ- and δ-cyanoketones
  作者：Tatsuya Shono、Naoki Kise

  DOI：10.1016/s0040-4039(00)88791-2

  日期：1990.1

  Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.

  在i-PrOH中电还原γ-和δ-氰基酮，生成环化产物α-羟基酮及其脱羟基酮，并将该反应用于二氢茉莉酮，二氢茉莉酮酸甲酯和Rosaprostol的合成。
• A Three-Component Coupling Approach to Cyclopentanoids
  作者：Barry M. Trost、Anthony B. Pinkerton

  DOI：10.1021/jo010593b

  日期：2001.11.1

  A new approach to 2,3-disubstituted cyclopentenones has been developed. This approach consists of a two-step protocol involving the cyclization of a Z-vinyl bromide under Barbier type conditions to form a cyclopentenol, which is then oxidatively rearranged to generate the cyclopentenone. The Z-vinyl bromide is in turn derived from a ruthenium catalyzed three-component coupling of an alkyne, an enone

  已经开发出一种新的2，3-二取代的环戊烯酮的方法。该方法由两步方案组成，涉及在Barbier型条件下将Z-乙烯基溴化物环化以形成环戊烯醇，然后将其氧化重排以生成环戊烯酮。Z-乙烯基溴化物又衍生自炔烃，烯酮和HBr等价物的钌催化的三组分偶联。已经产生了各种2，3-二取代的环戊烯酮，包括茉莉酮和二氢茉莉酮的短合成。该策略的进一步适用性在四氢二烯酮B，罗沙前列醇和选择性COX-2抑制剂的总合成中显示。
• A New Strategy for Cyclopentenone Synthesis
  作者：Barry M. Trost、Anthony B. Pinkerton

  DOI：10.1021/ol005853a

  日期：2000.6.1

  [reaction--see text] A new strategy for the synthesis of 2,3-disubstituted cyclopentenones emerges from two key reactions-the ruthenium-catalyzed three-component coupling of an equivalent of HBr, an alkyne, and a vinyl ketone and the Ni-Cr Barbier type reaction. As a result, these important structures are readily accessed from an alkyne and a vinyl ketone (which derive directly from carboxylic acids)

  [反应-见正文]由两个关键反应产生了一种合成2,3-二取代的环戊烯酮的新策略-钌催化的三组分相当于HBr，炔烃和乙烯基酮与Ni的三组分偶联-Cr Barbier型反应。结果，很容易从炔烃和乙烯基酮（它们直接衍生自羧酸）获得这些重要的结构。四氢二烯酮B和罗沙前列醇的合成说明了该新策略。
• Synthesis of (±)-Homosarkomycin and (±)-Rosaprostol
  作者：Shinji Tanimori、Tsutomu kainuki、Mitsuru Nakayama

  DOI：10.1271/bbb.56.1807

  日期：1992.1

  (+/-)-Homosarkomycin (2) and (+/-)-rosaprostol (3) were synthesized from (+/-)-methyl 2-oxo-bicyclo-[3.1.0]hexane-1-carboxylate (1) by using the nucleophilic ring opening reaction on the double-activated cyclopropane ring as the key step.

  (±)-Homosarkomycin (2) 和 (±)-rosaprostol (3) 是从 (±)-甲基 2-氧双环-[3.1.0]己烷-1-羧酸酯 (1) 合成的，其中利用双活化环丙烷环的亲核开环反应作为关键步骤。
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.