2-pentadecenoic acid | 75702-47-5

• 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: 2-pentadecenoic acid
• 英文别名: methyl trans-2-pentadecenoate；Methyl pentadecenoate；methyl (E)-pentadec-2-enoate
• CAS: 75702-47-5
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: TXPHRSOHMTXRQW-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-pentadecenoic acid 在 氢气 作用下， 生成 十五烷酸甲酯
  参考文献：
  名称：

  New irritant diterpene-esters from roots of L. (Euphorbiaceae)

  摘要：

  DOI：

  10.1016/s0040-4039(00)78635-7
• 作为产物：
  描述：

  十三醛 、 甲氧羰基亚甲基三苯基正膦 以 四氢呋喃 为溶剂， 反应 10.0h， 以97%的产率得到2-pentadecenoic acid
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345

文献信息

• METHODS OF REFINING AND PRODUCING FUEL AND SPECIALTY CHEMICALS FROM NATURAL OIL FEEDSTOCKS
  申请人：Cohen Steven A.

  公开号：US20130035502A1

  公开（公告）日：2013-02-07

  Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock with a low-molecular-weight olefin or mid-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.

  提供了一种精制天然油料的方法。该方法包括在存在交换催化剂的条件下，将油料与低分子量烯烃或中分子量烯烃反应，以形成包含烯烃和酯的交换产物。在某些实施例中，该方法还包括将交换产物中的烯烃与酯分离。在某些实施例中，该方法还包括在醇存在下对酯进行酯交换反应，以形成酯交换产物。
• METHODS OF REFINING AND PRODUCING DIBASIC ESTERS AND ACIDS FROM NATURAL OIL FEEDSTOCKS
  申请人：Snead Thomas E.

  公开号：US20130085288A1

  公开（公告）日：2013-04-04

  Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  提供了一种提炼天然油原料和生产二元酯和/或二元酸的方法。该方法包括在存在交换催化剂的情况下，将末端烯烃与内部烯烃反应，形成二元酯和/或二元酸。在某些实施例中，通过在存在交换催化剂的条件下反应原料来形成烯烃酯，以形成包含烯烃和酯的交换产物，将烯烃与酯从交换产物中分离，并在存在醇的情况下对酯进行酯交换反应，形成具有烯烃酯的酯交换产物。
• METHODS OF REFINING AND PRODUCING ISOMERIZED FATTY ACID ESTERS AND FATTY ACIDS FROM NATURAL OIL FEEDSTOCKS
  申请人：ELEVANCE RENEWABLE SCIENCES, INC.

  公开号：US20130204022A1

  公开（公告）日：2013-08-08

  Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

  提供了一种精制天然油原料和生产异构酯和酸的方法。该方法包括提供C4-C18不饱和脂肪酸酯或酸，并在热或异构化催化剂存在下异构化脂肪酸酯或酸以形成异构化脂肪酸酯或酸。在某些实施例中，该方法包括在异构化步骤之前形成二元酯或二元酸。在某些实施例中，该方法进一步包括水解二元酯以形成二元酸。在某些实施例中，烯烃是通过在丙烯酸酯催化剂存在下反应原料以形成包含烯烃和酯的交换产物，从交换产物中分离烯烃和酯，然后在醇存在下对酯进行酯交换反应以形成具有不饱和酯的酯交换产物来形成的。
• Methods of Refining and Producing Fuel and Specialty Chemicals from Natural Oil Feedstocks
  申请人：Elevance Renewable Sciences, Inc.

  公开号：US20140336399A1

  公开（公告）日：2014-11-13

  Methods are provided for refining natural oil feedstocks. The methods include reacting the feedstock with a molar excess of low-molecular-weight olefins in the presence of a metathesis catalyst. In certain embodiments, the methods further include separating at least a portion of the unreacted low-molecular-weight olefins. In certain embodiments, the methods further include recycling the separated unreacted low-molecular-weight olefins.

  提供了一种精制天然油原料的方法。该方法包括在存在交换催化剂的情况下，将原料与低分子量烯烃的摩尔过量反应。在某些实施例中，该方法还包括分离至少部分未反应的低分子量烯烃。在某些实施例中，该方法还包括回收分离的未反应的低分子量烯烃。
• Methods of Refining and Producing Dibasic Esters and Acids from Natural Oil Feedstocks
  申请人：Elevance Renewable Sciences, Inc.

  公开号：US20150299613A1

  公开（公告）日：2015-10-22

  Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  提供了一种精炼天然油原料和生产二元酯和/或二元酸的方法。该方法包括在存在交换催化剂的情况下，将末端烯烃与内部烯烃反应，形成二元酯和/或二元酸。在某些实施例中，通过在存在交换催化剂的条件下反应原料，以形成包含烯烃和酯的交换产物，从中分离烯烃和酯，并在醇的存在下对酯进行转酯化反应，以形成具有烯烃酯的转酯化产物。