methyl (Z)-2-tetracenoate | 75702-53-3

• 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: methyl (Z)-2-tetracenoate
• 英文别名: methyl (Z)-tetradec-2-enoate；Methyl (Z)-2-tetradecenoate
• CAS: 75702-53-3
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: CKTWGIPZKUEHIY-YPKPFQOOSA-N

物化性质

• 沸点：
  308.5±11.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl (Z)-2-tetracenoate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 cis-2-tetradecenoic acid
  参考文献：
  名称：

  Separation and synthesis of the new DSFs

  摘要：

  The three active compounds of DSF (the diffusible signal factor) family were purified from the culture fluid of rpfC (enzyme for DSF biosynthesis) mutated Xac (X. axonopo-dis pvciWi). These structures were characterized by C-13 NMR, H-1 NMR, HMBC, COSY, HMQC, MS-ESI, and named as (Z)-2-tetradecenoic acid (EDSF), (Z)-13-methyl-2-tetradecenoic acid (FDSF) and (Z)-12-methyl-2-tetradecenoic acid (GDSF). Also, starting from the corresponding tetradecanal or its homologue, three DSFs were synthesized by two steps to confirm the molecular structures. Finally, the X-gluc (the solution of 5-Bromo-4-chloro-3-indolyl-beta-D-glucuronidecyclohexylam monium salt) activities of these DSFs were tested, and the activity of the compounds can be listed as follows, form the most active compound to the least active compound, FDSF>GDSF>EDSF.

  DOI：

  10.33224/rrch.2020.65.4.10
• 作为产物：
  描述：

  Decylmagnesium bromide 在 copper(I) bromide dimethylsulfide complex 、 sodium hydride 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 生成 methyl (Z)-2-tetracenoate
  参考文献：
  名称：

  Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate

  摘要：

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.

  DOI：

  10.1021/jo00028a011

文献信息

• Mahipal Reddy; Raj Gopal; Jayathirtha Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 312 - 317
  作者：Mahipal Reddy、Raj Gopal、Jayathirtha Rao

  DOI：——

  日期：——
• Aciculitins A−C:  Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge <i>Aciculites </i><i>orientalis</i>
  作者：Carole A. Bewley、Haiyin He、David H. Williams、D. John Faulkner

  DOI：10.1021/ja953628w

  日期：1996.1.1

  The lithistid sponge Aciculites orientalis contains three cyclic peptides, aciculitins A-C (1-3), that are identical except for homologous lipid residues. The structure of the major peptide, aciculitin B (2), was elucidated by interpretation of spectroscopic data. The aciculitins consist of a bicyclic peptide that contains an unusual histidino-tyrosine bridge. Attached to the bicyclic peptide are C-13-C-15 2,3-dihydroxy-4,6-dienoic acids bearing D-lyxose at the 3-position. The structures of aciculitamides A (4) and B (5), which are artifacts obtained earlier from this sponge, are also presented. The aciculitins 1--3 inhibited the growth of Candida albicans and were cytotoxic toward the HCT-116 cell line.
• Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate
  作者：Douglass F. Taber、Michael J. Hennessy、James P. Louey

  DOI：10.1021/jo00028a011

  日期：1992.1

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.
• Separation and synthesis of the new DSFs
  作者：Chun-Bin TAN、Chang-Qin CHANG、Chun-Lan HE、Lian-Hui ZHANG、Xiao-Ling LIU

  DOI：10.33224/rrch.2020.65.4.10

  日期：——

  The three active compounds of DSF (the diffusible signal factor) family were purified from the culture fluid of rpfC (enzyme for DSF biosynthesis) mutated Xac (X. axonopo-dis pvciWi). These structures were characterized by C-13 NMR, H-1 NMR, HMBC, COSY, HMQC, MS-ESI, and named as (Z)-2-tetradecenoic acid (EDSF), (Z)-13-methyl-2-tetradecenoic acid (FDSF) and (Z)-12-methyl-2-tetradecenoic acid (GDSF). Also, starting from the corresponding tetradecanal or its homologue, three DSFs were synthesized by two steps to confirm the molecular structures. Finally, the X-gluc (the solution of 5-Bromo-4-chloro-3-indolyl-beta-D-glucuronidecyclohexylam monium salt) activities of these DSFs were tested, and the activity of the compounds can be listed as follows, form the most active compound to the least active compound, FDSF>GDSF>EDSF.