(R)-2-(Tetrahydro-pyran-2-yloxy)-butyraldehyde | 595583-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (R)-2-(Tetrahydro-pyran-2-yloxy)-butyraldehyde
• 英文别名: (2R)-2-(oxan-2-yloxy)butanal
• CAS: 595583-77-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: AYZNJYXHHXXRDW-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 、 (R)-2-(Tetrahydro-pyran-2-yloxy)-butyraldehyde 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以100%的产率得到(Z)-(R)-4-(Tetrahydro-pyran-2-yloxy)-hex-2-enoic acid methyl ester
  参考文献：
  名称：

  Us-7和-8的第一个不对称全合成，新的D-seco Corynanthe型虫生物碱：Us-7的结构修订和绝对立体化学的确定。

  摘要：

  [反应：见正文]从（S）-缩水甘油开始，完成了新型D-seco Corynanthe型氧吲哚Us-7和Us-8的不对称全合成。Us-7的结构从报道的结构（3R，7S）修订为结构22（3S，7R），并建立了两种生物碱在C15的绝对立体化学。

  DOI：

  10.1021/ol035128a
• 作为产物：
  描述：

  (R)-butane-1,2-diol 2-tetrahydropyranyl ether 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到(R)-2-(Tetrahydro-pyran-2-yloxy)-butyraldehyde
  参考文献：
  名称：

  Us-7和-8的第一个不对称全合成，新的D-seco Corynanthe型虫生物碱：Us-7的结构修订和绝对立体化学的确定。

  摘要：

  [反应：见正文]从（S）-缩水甘油开始，完成了新型D-seco Corynanthe型氧吲哚Us-7和Us-8的不对称全合成。Us-7的结构从报道的结构（3R，7S）修订为结构22（3S，7R），并建立了两种生物碱在C15的绝对立体化学。

  DOI：

  10.1021/ol035128a

文献信息

• Retiferol derivatives and their use in the treatment of skin diseases or conditions associated with photodamage
  申请人：——

  公开号：US20040077728A1

  公开（公告）日：2004-04-22

  Disclosed are retiferol derivatives of formula (I): wherein X is >C═CH 2 or —CH 2 —; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —O(CH 2 ) 3 —, —(CH 2 ) 2 -( 1,2 -C 6 H 4 )—, —CH═CH—( 1,2 -C 6 H 4 )—, —C═C—( 1,2 C 6 H 4 )—, —(CH 2 ) 2 —CO—, —CH 2 —O—CO—, —CH 2 NHCO—, or —CH 2 NHCOCH 2 —; R 1 is C 1 -C 5 -alkyl; R 2 and R 3 are independently of each other alkyl or perfluoroalkyl; and R 4 is hydrogen, hydroxy, C 1 -C 5 -alkyl or C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy; the use of such compounds to treat or present hyperproliferative skin diseases such as psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; neoplastic diseases; disorders of the sebaceous glands such as acne and seborrhoic dermatitis; the use of these compounds in reversing the conditions associated with photodamage, particularly for the oral or topical treatment of the skin damaged through sun exposure, the effects of wrinkling, elastosis and premature ageing, furthermore a process for the manufacture of such compounds as well as pharmaceutical compositions containing such compounds.

  揭示了化学式(I)的视黄醇衍生物，其中X是>C═CH2或—CH2—；Y和Z分别是氢、氟或羟基；A是—O(CH2)3—、—(CH2)2-(1,2-C6H4)—、—CH═CH—(1,2-C6H4)—、—C═C—(1,2C6H4)—、—(CH2)2—CO—、—CH2—O—CO—、—CH2NHCO—或—CH2NHCOCH2—；R1是C1-C5-烷基；R2和R3分别是烷基或全氟烷基；R4是氢、羟基、C1-C5-烷基或C1-C5-烷氧基；这些化合物的用途是治疗或预防过度增生性皮肤疾病，如银屑病、基底细胞癌、角化病和角化症；肿瘤性疾病；皮脂腺疾病，如痤疮和脂溢性皮炎；这些化合物用于逆转与光损伤相关的状况，特别是用于口服或局部治疗因日晒而受损的皮肤，以及对皱纹、弹性组织变性和过早衰老的影响；此外，还提供了制备这些化合物的方法以及含有这些化合物的药物组合物。
• RETIFEROL DERIVATIVES AND THEIR USE IN THE TREATMENT OF SKIN DISEASES OR CONDITIONS ASSOCIATED WITH PHOTODAMAGE
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1341745A1

  公开（公告）日：2003-09-10
• [EN] RETIFEROL DERIVATIVES AND THEIR USE IN THE TREATMENT OF SKIN DISEASES OR CONDITIONS ASSOCIATED WITH PHOTODAMAGE<br/>[FR] DERIVES DE RETIFEROL ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES DE PEAU OU DE TROUBLES ASSOCIES A DES DOMMAGES PHOTO-INDUITS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002042247A1

  公开（公告）日：2002-05-30

  Disclosed are retiferol derivatives of formula (I): wherein X is > C=CH2 or -CH2-; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is -O(CH2)3-, -(CH2)2-(1,2-C6H4)-, -CH=CH-(1,2-C6H4)-, -C=C-(1,2-C6H4)-, -(CH2)2-CO-, -CH2-O-CO-, -CH2NHCO-, or -CH2NHCOCH2-; R1 is C1-C5-alkyl; R?2 and R3¿ are independently of each other alkyl or perfluoroalkyl; and R4 is hydrogen, hydroxy, C1-C5-alkyl or C1-C5-alkyl or C1-C5-alkoxy; the use of such compounds to treat or present hyperproliferative skin diseases such as psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; neoplastic diseases; disorders of the sebaceous glands such as acne and seborrhoic dermatitis; the use of these compounds in reversing the conditions associated with photodamage, particularly for the oral or topical treatment of the skin damaged through sun exposure, the effects of wrinkling, elastosis and premature ageing, furthermore a process for the manufacture of such compounds as well as pharmaceutical compositions containing such compounds.
• First Asymmetric Total Synthesis of Us-7 and -8, Novel <i>D</i>-<i>s</i><i>eco</i> Corynanthe-Type Oxindole Alkaloids from <i>Uncaria </i><i>a</i><i>ttenuata</i>:  Structure Revision of Us-7 and Determination of Absolute Stereochemistry
  作者：Hiromitsu Takayama、Rika Fujiwara、Yasuko Kasai、Mariko Kitajima、Norio Aimi

  DOI：10.1021/ol035128a

  日期：2003.8.1

  [reaction: see text] Starting from (S)-glycidol, the asymmetric total synthesis of novel D-seco Corynanthe-type oxindoles Us-7 and Us-8 was accomplished. The structure of Us-7 was revised from the reported structure 1 with the (3R,7S) form to structure 22 with (3S,7R), and the absolute stereochemistry at C15 of both alkaloids was established.

  [反应：见正文]从（S）-缩水甘油开始，完成了新型D-seco Corynanthe型氧吲哚Us-7和Us-8的不对称全合成。Us-7的结构从报道的结构（3R，7S）修订为结构22（3S，7R），并建立了两种生物碱在C15的绝对立体化学。