geranyl farnesol | 79577-58-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: geranyl farnesol
• 英文别名: 3,7,11,15,19-pentamethyl-eicosa-2,6,10,14,18-pentaen-1-ol；3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-ol
• CAS: 79577-58-5
• 化学式: C₂₅H₄₂O
• 分子量: 358.608
• InChiKey: YHTCXUSSQJMLQD-UHFFFAOYSA-N

物化性质

• 沸点：
  466.6±14.0 °C(Predicted)
• 密度：
  0.883±0.06 g/cm3(Predicted)
• LogP：
  8.602 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  geranyl farnesol 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 正丁基锂 、 三溴化磷 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.67h， 生成 2-(3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methyl-naphthalene
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF VITAMIN K2
  [FR] PROCÉDÉ DE PRÉPARATION DE LA VITAMINE K2

  摘要：

  公开号：

  WO2011117324A3

文献信息

• [EN] CRYSTALLINE MENOQUINONE-7 (VITAMIN K2)<br/>[FR] MENOQUINONE-7 CRISTALLINE (VITAMINE K2)
  申请人：KAPPA BIOSCIENCE AS

  公开号：WO2010034999A1

  公开（公告）日：2010-04-01

  A compound of formula (I) in solid form, preferably crystalline form.

  公式为（I）的化合物，最好是固体形式，尤其是结晶形式。
• PROCESS FOR THE PREPARATION OF VITAMIN K2
  申请人：Skattebol Lars

  公开号：US20110207967A1

  公开（公告）日：2011-08-25

  Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I) is defined including a step in which (i) a compound of formula (II) is reacted formula (III) wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

  通过 Kumada、Suzuki 和 Biellmann 化学反应的组合，可以快速合成各种维生素K2成分的甲萘醌，具有立体化学完整性，为制备这些成分进入药品市场提供了新的途径。在一种实施例中，定义了一种制备公式（I）化合物的过程，其中包括以下步骤：（i）在铜、镍或钯催化剂的存在下，将公式（II）化合物和公式（III）化合物反应，其中 R 是烷基；LG 是离去基团；m 是从0到8的整数；n 是从0到9的整数；X 是氢、卤素、羟基或保护羟基。
• Use of (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid for the treatment of leukaemia
  申请人：Eisai Co., Ltd.

  公开号：EP0614662A1

  公开（公告）日：1994-09-14

  To provide a remedy or ameliorant, based on the effect of inducing cell differentiation, for diseases such as hematopoietic organ tumors and solid tumors for which no clinically highly useful drug has been known hitherto. The fundamental idea of the conventional pharmacotherapy for cancer resides in completely exterminating tumor cells having an unusually high capability of multiplication. However these treatments also had toxicities against normal cells and thus grave side effects were unavoidable. Further, only limited therapeutic effects could be achieved. On the other hand, although all-transretinoic acid had a remarkable effect on acute promyelocytic leukemia, there was reported that this compound also had grave side effects. Further, there was another problem that the diseases tended to recur after it was healed. In contrast, (2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid has an unexpected effect of inducing cell differentiation and a high safety. Being different in structure from all-trans-retinoic acid, this compound has a high possibility of preventing the recurrence of the disease. Therefore, it is expected as a clinically useful remedy or ameliorant for hematopoietic organ tumors, in particular, acute promyelocytic leukemia and myeloid dysplasia syndrome.

  提供一种基于诱导细胞分化效应的疗法或改善剂，用于治疗造血器官肿瘤和实体瘤等疾病，迄今为止，尚未发现任何临床上非常有用的药物。传统的癌症药物疗法的基本理念是彻底消灭具有超常繁殖能力的肿瘤细胞。然而，这些疗法对正常细胞也有毒性，因此不可避免地会产生严重的副作用。此外，只能取得有限的治疗效果。另一方面，虽然全反式维甲酸对急性早幼粒细胞白血病有显著疗效，但据报道这种化合物也有严重的副作用。此外，还有一个问题是，疾病在治愈后往往会复发。相比之下，(2E,4E,6E,10E)-3,7,11,15-四甲基-2,4,6,10,14-十六碳五烯酸在诱导细胞分化方面具有意想不到的效果，而且安全性很高。由于其结构与全反式维甲酸不同，这种化合物极有可能防止疾病复发。因此，它有望成为造血器官肿瘤，特别是急性早幼粒细胞白血病和骨髓增生异常综合征的临床有效治疗剂或改善剂。
• Process for producing all trans-form polyprenols
  申请人：KURARAY CO., LTD.

  公开号：EP0771778A2

  公开（公告）日：1997-05-07

  An all trans-form polyprenol is obtained by; (A) subjecting a 3,7-dimethyl-6-hydroxy-7-octen-1-ol derivative to five-carbon lengthening reaction m-times which comprises reacting with 2-methyl-3,3-dimethoxy-1-butene and reducing the carbonyl group of the resulting compound, to obtain an allyl alcohol derivative; (B) halogenating the hydroxyl group of the allyl alcohol derivative to convert it to form an allyl halide derivative; (C) allowing the allyl halide derivative to react with a polyisoprenyl sulfone derivative to form a sulfonated polyprenol derivative; and (D) subjecting the sulfonated polyprenol derivative to desulfonylation to obtain the all trans-form polyprenol.

  通过以下方法可以得到全反式多酚； (A) 将 3,7-二甲基-6-羟基-7-辛烯-1-醇衍生物进行五碳延长反应 m 次，包括与 2-甲基-3,3-二甲氧基-1-丁烯反应，并还原所得化合物的羰基，以获得烯丙醇衍生物； (B) 卤化烯丙醇衍生物的羟基，将其转化为烯丙基卤化物衍生物； (C) 让烯丙基卤化物衍生物与聚异戊烯基砜衍生物反应，形成磺化聚丙 烯醇衍生物；以及 (D) 将磺化聚丙稀酚衍生物进行脱磺化反应，得到全反式聚丙稀酚。
• A process for preparing all trans-form polyprenols
  申请人：Kuraray Co., Ltd.

  公开号：EP1031551A2

  公开（公告）日：2000-08-30

  The invention refers to a process comprising treating a compound represented by Formula (202):    wherein p and q each represent an integer of 0 or 1 or more; Y and Z each represent a hydrogen atom, or combine to form a carbon-carbon bond; R1 represents an alkyl group or an aryl group; and A represents a protective group of the hydroxyl group; with an alkali metal and a polycyclic aromatic compound to produce a compound represented by Formula (201): wherein p, q, Y and Z are as defined above; and R2 represents a hydrogen atom or the same protective group of the hydroxyl group as that represented by A.

  本发明涉及一种工艺，包括处理由式（202）代表的化合物： 其中 p 和 q 分别代表 0 或 1 或更多的整数；Y 和 Z 分别代表氢原子，或结合成碳-碳键；R1 代表烷基或芳基；A 代表羟基的保护基团； 用碱金属和多环芳烃化合物生成由式（201）表示的化合物： 其中 p、q、Y 和 Z 如上定义；R2 代表氢原子或与 A 所代表的羟基相同的保护基团。