(E)-tetradec-2-enoyl chloride | 59044-31-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-tetradec-2-enoyl chloride
• CAS: 59044-31-4
• 化学式: C₁₄H₂₅ClO
• 分子量: 244.805
• InChiKey: YLSIKYJGOAZUCW-OUKQBFOZSA-N

物化性质

• 沸点：
  317.4±11.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-tetradec-2-enoyl chloride 在 吡啶 、 AD-mix-α 、 甲基磺酰胺 、 sodium sulfite 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Aciculitins A−C:  Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge Aciculites orientalis

  摘要：

  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.

  DOI：

  10.1021/ja953628w
• 作为产物：
  描述：

  十二醛 在 甲醇 、 lithium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 (E)-tetradec-2-enoyl chloride
  参考文献：
  名称：

  Aciculitins A−C:  Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge Aciculites orientalis

  摘要：

  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.

  DOI：

  10.1021/ja953628w

文献信息

• Inhibitory effect of 2-(E-2-alkenoylamino)ethyl alkyl sulfides on gastric ulceration in rats. I. Effect of 2-(E-2-alkenoylamino)ethyl carbamoylmethyl sulfides on gastric secretion and various ulceration models in rats.
  作者：MASAKAZU IWAI、ISAO KOHDA、CHIKARA FUKAYA、YOICHIRO NAITO、KAZUMASA YOKOYAMA、HIROSHI NAKAJIMA、KAZUTAKE TSUJIKAWA、MASARU OKABE、TSUTOMU MIMURA

  DOI：10.1248/cpb.35.4616

  日期：——

  Bis [2- (E-2-alkenoylaminoethyl)] disulfides (I) and 2- (E-2-alkenoylamino) ethyl carbamoylmethyl sulfides (II) with various alkenyl chain lengths were synthesized and their inhibitory effects on gastric secretion in rats were compared. There was a relationship between the alkenyl chain length of a series of sulfide derivatives (II) and their biological activities (C10 and C11 alkenyl derivatives were the most effective compounds). On the other hand, variation of the alkenyl chain length did not affect the anti-ulcerogenic activity of the disulfide derivatives (I). The derivatives (II) showed stronger biological activity than (I) when the same alkenyl group was present in both. The administration of 2- (E-2-decenoylamino) ethyl carbamoylmethyl sulfide (II-5) or 2- (E-2-undecenoylamino) ethyl carbamoylmethyl sulfide (II-6) at a dose of 20 mg/kg (i.p.) caused significant inhibition of various experimental ulcerations caused by stress, aspirin and HCl-ethanol. Oral administration of both acetamides (II-5, II-6) also caused 50-60% inhibition of ulceration in the water-immersion stress model at a dose of 20 mg/kg, although the activity was not as strong as that after i.p. injection. An improvement in anti-ulcerogenic activity was observed when acetamides were administered as a suspension in 10% HCO-60. Both acetamides (II-5, II-6) caused a dose-dependent decrease of the ulcer index of restrained and water-immersion stress-loaded rats in the dosage range from 0.5 mg/kg p.o. to 5 mg/kg p.o. The lethal dose 50% values (LD50) for both acetamides were over 8 g/kg (p.o. or i.p.).

  合成了各种烯烃链长度的双[2-(E-2-烯酰氨基乙基)]二硫化物 (I) 和 2-(E-2-烯酰氨基)乙基氨基甲基硫化物 (II)，并比较了它们对大鼠胃分泌的抑制作用。硫化物衍生物 (II) 的生物活性与烯烃链的长度之间存在一定关系（C10 和 C11 烯烃衍生物是最有效的化合物）。另一方面，烯烃链长度的变化并未影响二硫化物衍生物 (I) 的抗溃疡活性。当两者具有相同的烯烃基时，衍生物 (II) 的生物活性比 (I) 更强。以 20 mg/kg（i.p.）的剂量给药 2-(E-2-癸烯酰氨基)乙基氨基甲基硫化物 (II-5) 或 2-(E-2-十一烯酰氨基)乙基氨基甲基硫化物 (II-6) 显著抑制了由压力、阿司匹林和盐酸-乙醇引起的各种实验性溃疡。以 20 mg/kg 的剂量口服两种醋酸胺 (II-5, II-6) 也在水浸应激模型中引起了 50-60% 的溃疡抑制，尽管其活性不及腹腔注射后的强。以 10% HCO-60 悬浮液给药时，观察到醋酸胺的抗溃疡活性有所改善。这两种醋酸胺 (II-5, II-6) 在 0.5 mg/kg p.o. 到 5 mg/kg p.o. 剂量范围内引起了被限制和水浸应激负荷大鼠的溃疡指数的剂量依赖性下降。这两种醋酸胺的半数致死剂量 (LD50) 均超过 8 g/kg（口服或腹腔注射）。
• NOVEL COMPOUNDS
  申请人：AVANTI POLAR LIPIDS, INC.

  公开号：US20160024001A1

  公开（公告）日：2016-01-28

  Disclosed are compounds of the general formula I and II (as further defined herein) are useful in the production of inhibitors of sphingolipid synthesis the production of sphingolipids. Suitable sphingolipids, include, but not limited to, sphingosine and compounds incorporating sphingosine or that may use sphingosine as an intermediate or a starting material in their synthesis (including, but not limited to, sphingosine-1-P, ceramide, gangliosides and sphigomyelin). In one contemplated use, compounds of the general formula I and II are useful in the production of sphingosine. In another contemplated use, compounds of the general formula I and II are useful in the production of a sphingofugin. Methods of manufacturing each of the above compounds are also provided.

  本发明公开了一般式I和II（如下文所定义）的化合物，其在制备鞘脂合成抑制剂和鞘脂的生产中有用。适当的鞘脂包括但不限于神经酰胺和包含神经酰胺或可能在其合成中使用神经酰胺作为中间体或起始材料的化合物（包括但不限于神经酰胺-1-P，鞘醇胺，神经节苷脂和鞘磷脂）。在一种考虑中，一般式I和II的化合物在制备神经酰胺方面有用。在另一种考虑中，一般式I和II的化合物在制备神经酰胺素方面有用。还提供了制造上述每种化合物的方法。
• Compounds
  申请人：Avanti Polar Lipids, Inc.

  公开号：US09403760B2

  公开（公告）日：2016-08-02

  Disclosed are compounds of the general formula I and II (as further defined herein) are useful in the production of inhibitors of sphingolipid synthesis the production of sphingolipids. Suitable sphingolipids, include, but not limited to, sphingosine and compounds incorporating sphingosine or that may use sphingosine as an intermediate or a starting material in their synthesis (including, but not limited to, sphingosine-1-P, ceramide, gangliosides and sphingomyelin). In one contemplated use, compounds of the general formula I and II are useful in the production of sphingosine. In another contemplated use, compounds of the general formula I and II are useful in the production of a sphingofugin. Methods of manufacturing each of the above compounds are also provided.

  公开了一般式I和II的化合物（在此进一步定义），这些化合物在生产鞘脂合成抑制剂和鞘脂的生产中非常有用。适合的鞘脂包括但不限于鞘氨醇和含有鞘氨醇或可能在其合成中使用鞘氨醇作为中间体或起始物质的化合物（包括但不限于鞘氨醇-1-P，神经节苷脂和鞘磷脂）。在一种考虑中，一般式I和II的化合物在鞘氨醇的生产中非常有用。在另一种考虑中，一般式I和II的化合物在生产鞘氨醇的生产中非常有用。还提供了制造上述每种化合物的方法。
• US2014/275591
  申请人：——

  公开号：——

  公开（公告）日：——
• US20140275591A1
  申请人：——

  公开号：——

  公开（公告）日：——