19-phenyl-1-nonadecanol | 218965-27-6

• 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: 19-phenyl-1-nonadecanol
• 英文别名: 19-Phenylnonadecan-1-ol
• CAS: 218965-27-6
• 化学式: C₂₅H₄₄O
• 分子量: 360.624
• InChiKey: KPEFXWNNQFYUJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  19-phenyl-1-nonadecanol 在 亚磷酸三苯酯 、 碘 、 lithium diisopropyl amide 作用下， 反应 23.67h， 生成 grandinolide
  参考文献：
  名称：

  Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin

  摘要：

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q
• 作为产物：
  描述：

  2-nonadecyn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal copper(l) iodide 、 potassium tert-butylate 、 氢气 、 lithium 、 1,2-丙二胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 25.0 ℃ 、500.0 kPa 条件下， 反应 29.0h， 生成 19-phenyl-1-nonadecanol
  参考文献：
  名称：

  Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin

  摘要：

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q

文献信息

• PAI-1 INHIBITOR
  申请人：Yamaguchi Youichi

  公开号：US20090312315A1

  公开（公告）日：2009-12-17

  The compound represented by the following formula (I) and the like have PAI-1 inhibition activity; wherein: R 1 represents a C 6-10 aryl group which may be substituted or the like; T represents a single bond or the like; m represents 0 or 1; when m is 0, G represents —N—C(═O)—CO 2 H or the like; when m is 1, G represents an oxygen atom or the like; R 2 represents a C 6-10 aryl group which may be substituted or the like; E represents the following formula (II) wherein one of R 31 , R 32 , R 33 and R 34 represents the formula R 1 -T-, each of the other three independently represents a hydrogen atom or the like, and R 35 represents the formula —X—Y′, a hydrogen atom or the like; X represents —CH 2 — or the like; Y′ represents a carboxy group or the like; M represents a single bond or the like.

  以下公式（I）表示的化合物及类似化合物具有PAI-1抑制活性；其中：R1代表可能被取代的C6-10芳基或类似基团；T代表单键或类似键；m代表0或1；当m为0时，G代表—N—C(═O)—CO2H或类似基团；当m为1时，G代表氧原子或类似基团；R2代表可能被取代的C6-10芳基或类似基团；E代表以下公式（II），其中R31、R32、R33和R34中的一个代表公式R1-T-，其余三个分别独立地代表氢原子或类似基团，R35代表公式—X—Y′，氢原子或类似基团；X代表—CH2—或类似基团；Y′代表羧基或类似基团；M代表单键或类似键。
• US8633245B2
  申请人：——

  公开号：US8633245B2

  公开（公告）日：2014-01-21